# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_L _database_code_depnum_ccdc_archive 'CCDC 904342' #TrackingRef '14433_web_deposit_cif_file_0_AlexanderLyakhov_1349292712.L.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H13 N5' _chemical_formula_sum 'C10 H13 N5' _chemical_formula_weight 203.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8402(6) _cell_length_b 10.5972(6) _cell_length_c 11.2157(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.8140(10) _cell_angle_gamma 90.00 _cell_volume 1043.80(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4710 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.93 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9669 _exptl_absorpt_correction_T_max 0.9833 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10272 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2392 _reflns_number_gt 2071 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2010)' _computing_data_reduction 'SAINT (Bruker, 2010)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material ; SHELXL-97 (Sheldrick, 2008), PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+0.2984P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2392 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.25385(10) -0.03103(8) 0.53259(9) 0.0176(2) Uani 1 1 d . . . N2 N 0.30789(10) 0.08010(8) 0.51966(8) 0.0159(2) Uani 1 1 d . . . N3 N 0.33090(10) 0.08882(9) 0.41218(9) 0.0193(2) Uani 1 1 d . . . N4 N 0.29041(11) -0.02160(8) 0.35041(9) 0.0195(2) Uani 1 1 d . . . C5 C 0.24413(11) -0.09280(10) 0.42552(10) 0.0156(2) Uani 1 1 d . . . C6 C 0.19240(11) -0.22516(10) 0.39944(10) 0.0155(2) Uani 1 1 d . . . N7 N 0.14086(11) -0.26699(8) 0.27320(9) 0.0197(2) Uani 1 1 d . . . C8 C 0.09495(13) -0.38768(11) 0.25069(11) 0.0212(2) Uani 1 1 d . . . H8 H 0.0604(15) -0.4170(12) 0.1600(13) 0.022(3) Uiso 1 1 d . . . C9 C 0.09761(12) -0.46916(10) 0.34859(11) 0.0207(2) Uani 1 1 d . . . H9 H 0.0623(16) -0.5545(13) 0.3242(13) 0.025(3) Uiso 1 1 d . . . C10 C 0.15097(12) -0.42403(10) 0.47799(11) 0.0193(2) Uani 1 1 d . . . H10 H 0.1539(16) -0.4761(13) 0.5483(14) 0.025(3) Uiso 1 1 d . . . C11 C 0.19892(11) -0.29953(10) 0.50413(10) 0.0167(2) Uani 1 1 d . . . H11 H 0.2364(15) -0.2642(12) 0.5928(13) 0.021(3) Uiso 1 1 d . . . C1 C 0.33273(12) 0.18440(10) 0.61738(10) 0.0175(2) Uani 1 1 d . . . C2 C 0.42813(13) 0.13055(11) 0.75678(11) 0.0225(2) Uani 1 1 d . . . H2A H 0.3747(15) 0.0618(13) 0.7774(13) 0.023(3) Uiso 1 1 d . . . H2B H 0.4474(16) 0.1992(13) 0.8214(14) 0.027(3) Uiso 1 1 d . . . H2C H 0.5230(16) 0.0973(13) 0.7639(13) 0.026(3) Uiso 1 1 d . . . C3 C 0.17585(12) 0.22622(11) 0.59897(12) 0.0207(2) Uani 1 1 d . . . H3A H 0.1210(16) 0.1551(13) 0.6152(14) 0.028(3) Uiso 1 1 d . . . H3B H 0.1131(16) 0.2590(13) 0.5070(14) 0.027(3) Uiso 1 1 d . . . H3C H 0.1884(15) 0.2929(13) 0.6642(14) 0.025(3) Uiso 1 1 d . . . C4 C 0.41569(14) 0.29219(11) 0.58848(13) 0.0247(3) Uani 1 1 d . . . H4A H 0.3562(17) 0.3273(14) 0.4993(15) 0.035(4) Uiso 1 1 d . . . H4B H 0.5144(17) 0.2669(13) 0.5967(14) 0.030(4) Uiso 1 1 d . . . H4C H 0.4317(16) 0.3603(14) 0.6553(15) 0.033(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0202(4) 0.0149(4) 0.0193(4) -0.0012(3) 0.0104(4) -0.0011(3) N2 0.0174(4) 0.0141(4) 0.0179(4) 0.0002(3) 0.0095(3) 0.0005(3) N3 0.0239(5) 0.0182(5) 0.0185(4) 0.0000(3) 0.0119(4) 0.0001(3) N4 0.0240(5) 0.0178(4) 0.0188(4) -0.0004(3) 0.0113(4) -0.0007(3) C5 0.0145(5) 0.0170(5) 0.0152(5) 0.0010(4) 0.0066(4) 0.0026(4) C6 0.0141(5) 0.0162(5) 0.0168(5) -0.0008(4) 0.0074(4) 0.0019(4) N7 0.0239(5) 0.0190(5) 0.0165(4) -0.0012(3) 0.0093(4) 0.0009(4) C8 0.0242(6) 0.0198(5) 0.0177(5) -0.0038(4) 0.0077(4) 0.0000(4) C9 0.0201(5) 0.0159(5) 0.0242(5) -0.0020(4) 0.0083(4) -0.0003(4) C10 0.0186(5) 0.0189(5) 0.0208(5) 0.0038(4) 0.0093(4) 0.0021(4) C11 0.0157(5) 0.0187(5) 0.0155(5) -0.0002(4) 0.0070(4) 0.0023(4) C1 0.0188(5) 0.0151(5) 0.0194(5) -0.0035(4) 0.0092(4) -0.0001(4) C2 0.0230(6) 0.0217(5) 0.0192(5) -0.0035(4) 0.0063(4) 0.0012(4) C3 0.0195(5) 0.0193(5) 0.0239(5) -0.0026(4) 0.0104(4) 0.0021(4) C4 0.0264(6) 0.0180(5) 0.0340(6) -0.0035(5) 0.0175(5) -0.0032(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.3268(12) . ? N1 C5 1.3326(13) . ? N2 N3 1.3263(12) . ? N2 C1 1.4969(13) . ? N3 N4 1.3263(13) . ? N4 C5 1.3537(13) . ? C5 C6 1.4758(14) . ? C6 N7 1.3456(13) . ? C6 C11 1.3914(14) . ? N7 C8 1.3419(14) . ? C8 C9 1.3877(16) . ? C8 H8 0.967(13) . ? C9 C10 1.3868(15) . ? C9 H9 0.964(14) . ? C10 C11 1.3872(15) . ? C10 H10 0.952(14) . ? C11 H11 0.967(13) . ? C1 C4 1.5215(15) . ? C1 C2 1.5255(15) . ? C1 C3 1.5279(14) . ? C2 H2A 0.985(14) . ? C2 H2B 0.984(14) . ? C2 H2C 0.966(15) . ? C3 H3A 0.991(14) . ? C3 H3B 0.995(14) . ? C3 H3C 0.984(14) . ? C4 H4A 0.976(15) . ? C4 H4B 0.971(15) . ? C4 H4C 1.001(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C5 101.94(8) . . ? N3 N2 N1 113.72(8) . . ? N3 N2 C1 125.14(8) . . ? N1 N2 C1 121.10(8) . . ? N4 N3 N2 106.21(8) . . ? N3 N4 C5 105.83(8) . . ? N1 C5 N4 112.30(9) . . ? N1 C5 C6 121.58(9) . . ? N4 C5 C6 126.10(9) . . ? N7 C6 C11 123.60(10) . . ? N7 C6 C5 117.02(9) . . ? C11 C6 C5 119.38(9) . . ? C8 N7 C6 116.55(9) . . ? N7 C8 C9 124.03(10) . . ? N7 C8 H8 115.6(8) . . ? C9 C8 H8 120.3(8) . . ? C10 C9 C8 118.46(10) . . ? C10 C9 H9 122.6(8) . . ? C8 C9 H9 119.0(8) . . ? C9 C10 C11 118.77(10) . . ? C9 C10 H10 121.5(8) . . ? C11 C10 H10 119.7(8) . . ? C10 C11 C6 118.59(10) . . ? C10 C11 H11 121.4(8) . . ? C6 C11 H11 120.0(8) . . ? N2 C1 C4 108.93(8) . . ? N2 C1 C2 107.21(8) . . ? C4 C1 C2 110.97(9) . . ? N2 C1 C3 107.09(8) . . ? C4 C1 C3 111.09(9) . . ? C2 C1 C3 111.35(9) . . ? C1 C2 H2A 111.7(8) . . ? C1 C2 H2B 107.7(8) . . ? H2A C2 H2B 108.6(11) . . ? C1 C2 H2C 110.3(8) . . ? H2A C2 H2C 108.0(11) . . ? H2B C2 H2C 110.5(11) . . ? C1 C3 H3A 110.8(8) . . ? C1 C3 H3B 111.0(8) . . ? H3A C3 H3B 108.7(11) . . ? C1 C3 H3C 109.1(8) . . ? H3A C3 H3C 107.9(11) . . ? H3B C3 H3C 109.3(11) . . ? C1 C4 H4A 111.9(9) . . ? C1 C4 H4B 112.5(9) . . ? H4A C4 H4B 108.3(12) . . ? C1 C4 H4C 107.5(8) . . ? H4A C4 H4C 108.1(12) . . ? H4B C4 H4C 108.4(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 N2 N3 0.06(11) . . . . ? C5 N1 N2 C1 177.83(8) . . . . ? N1 N2 N3 N4 -0.01(11) . . . . ? C1 N2 N3 N4 -177.68(9) . . . . ? N2 N3 N4 C5 -0.03(11) . . . . ? N2 N1 C5 N4 -0.08(11) . . . . ? N2 N1 C5 C6 178.17(9) . . . . ? N3 N4 C5 N1 0.07(12) . . . . ? N3 N4 C5 C6 -178.07(9) . . . . ? N1 C5 C6 N7 159.71(10) . . . . ? N4 C5 C6 N7 -22.30(15) . . . . ? N1 C5 C6 C11 -20.28(14) . . . . ? N4 C5 C6 C11 157.70(10) . . . . ? C11 C6 N7 C8 -0.39(15) . . . . ? C5 C6 N7 C8 179.61(9) . . . . ? C6 N7 C8 C9 0.17(16) . . . . ? N7 C8 C9 C10 -0.09(17) . . . . ? C8 C9 C10 C11 0.21(16) . . . . ? C9 C10 C11 C6 -0.41(15) . . . . ? N7 C6 C11 C10 0.52(16) . . . . ? C5 C6 C11 C10 -179.48(9) . . . . ? N3 N2 C1 C4 -10.49(13) . . . . ? N1 N2 C1 C4 172.01(9) . . . . ? N3 N2 C1 C2 -130.64(10) . . . . ? N1 N2 C1 C2 51.85(12) . . . . ? N3 N2 C1 C3 109.75(11) . . . . ? N1 N2 C1 C3 -67.76(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C11 H11 N7 0.967(13) 2.608(13) 3.3890(14) 138.0(10) 4_556 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.272 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.043 data_1 _database_code_depnum_ccdc_archive 'CCDC 904343' #TrackingRef '14434_web_deposit_cif_file_1_AlexanderLyakhov_1349292712.1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H26 Cl2 Cu N10' _chemical_formula_sum 'C20 H26 Cl2 Cu N10' _chemical_formula_weight 540.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P c' _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 10.2378(8) _cell_length_b 8.6284(7) _cell_length_c 14.6102(12) _cell_angle_alpha 90.00 _cell_angle_beta 110.1260(10) _cell_angle_gamma 90.00 _cell_volume 1211.80(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8486 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 29.04 _exptl_crystal_description prism _exptl_crystal_colour cyan _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 558 _exptl_absorpt_coefficient_mu 1.152 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7617 _exptl_absorpt_correction_T_max 0.8742 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11589 _diffrn_reflns_av_R_equivalents 0.0140 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5393 _reflns_number_gt 5213 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2010)' _computing_data_reduction 'SAINT (Bruker, 2010)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material ; SHELXL-97 (Sheldrick, 2008), PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.4910P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.311(9) _refine_ls_number_reflns 5393 _refine_ls_number_parameters 305 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0860 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.21503(3) 0.28215(4) 0.71139(2) 0.01617(8) Uani 1 1 d . . . Cl1 Cl 0.04566(6) 0.17673(8) 0.76562(4) 0.02019(13) Uani 1 1 d . . . Cl2 Cl 0.38307(6) 0.39155(7) 0.65762(4) 0.02007(14) Uani 1 1 d . . . N11 N -0.0831(2) 0.6130(3) 0.53627(16) 0.0195(5) Uani 1 1 d . . . N21 N -0.1187(2) 0.5148(3) 0.46117(16) 0.0175(4) Uani 1 1 d . . . N31 N -0.0473(2) 0.3841(2) 0.47989(16) 0.0178(4) Uani 1 1 d . . . N41 N 0.0402(2) 0.3952(3) 0.57034(16) 0.0176(4) Uani 1 1 d . . . C51 C 0.0165(3) 0.5346(3) 0.60281(18) 0.0153(5) Uani 1 1 d . . . C11 C -0.2426(3) 0.5385(3) 0.37031(18) 0.0206(6) Uani 1 1 d . . . C21 C -0.3676(3) 0.4739(4) 0.3923(3) 0.0322(7) Uani 1 1 d . . . H21A H -0.3621 0.3606 0.3951 0.048 Uiso 1 1 calc R . . H21B H -0.4536 0.5056 0.3408 0.048 Uiso 1 1 calc R . . H21C H -0.3672 0.5143 0.4551 0.048 Uiso 1 1 calc R . . C31 C -0.2157(4) 0.4572(5) 0.2869(2) 0.0471(11) Uani 1 1 d . . . H31A H -0.1305 0.4984 0.2798 0.071 Uiso 1 1 calc R . . H31B H -0.2943 0.4747 0.2265 0.071 Uiso 1 1 calc R . . H31C H -0.2048 0.3458 0.3004 0.071 Uiso 1 1 calc R . . C41 C -0.2601(3) 0.7113(3) 0.3507(2) 0.0221(5) Uani 1 1 d . . . H41A H -0.2747 0.7630 0.4062 0.033 Uiso 1 1 calc R . . H41B H -0.3407 0.7296 0.2917 0.033 Uiso 1 1 calc R . . H41C H -0.1763 0.7529 0.3418 0.033 Uiso 1 1 calc R . . C61 C 0.0928(2) 0.5911(3) 0.70235(18) 0.0144(5) Uani 1 1 d . . . N71 N 0.1828(2) 0.4880(3) 0.76176(15) 0.0156(4) Uani 1 1 d . . . C81 C 0.2525(3) 0.5300(3) 0.85378(19) 0.0185(5) Uani 1 1 d . . . H81 H 0.3163 0.4586 0.8954 0.022 Uiso 1 1 calc R . . C91 C 0.2355(3) 0.6743(3) 0.89100(19) 0.0196(5) Uani 1 1 d . . . H91 H 0.2843 0.6998 0.9573 0.024 Uiso 1 1 calc R . . C101 C 0.1451(3) 0.7800(3) 0.8288(2) 0.0185(6) Uani 1 1 d . . . H101 H 0.1330 0.8801 0.8516 0.022 Uiso 1 1 calc R . . C111 C 0.0730(3) 0.7377(3) 0.73312(19) 0.0173(5) Uani 1 1 d . . . H111 H 0.0110 0.8084 0.6895 0.021 Uiso 1 1 calc R . . N12 N 0.5218(2) -0.0555(3) 0.87973(15) 0.0168(4) Uani 1 1 d . . . N22 N 0.5579(2) 0.0361(3) 0.95712(15) 0.0160(4) Uani 1 1 d . . . N32 N 0.4854(2) 0.1667(3) 0.94460(16) 0.0187(5) Uani 1 1 d . . . N42 N 0.3971(2) 0.1622(3) 0.85395(16) 0.0177(4) Uani 1 1 d . . . C52 C 0.4208(2) 0.0267(3) 0.81614(19) 0.0150(5) Uani 1 1 d . . . C12 C 0.6699(3) -0.0107(3) 1.05088(18) 0.0189(5) Uani 1 1 d . . . C22 C 0.8008(3) -0.0458(4) 1.0279(2) 0.0268(6) Uani 1 1 d . . . H22A H 0.7811 -0.1272 0.9783 0.040 Uiso 1 1 calc R . . H22B H 0.8743 -0.0809 1.0873 0.040 Uiso 1 1 calc R . . H22C H 0.8314 0.0482 1.0035 0.040 Uiso 1 1 calc R . . C32 C 0.6946(3) 0.1238(4) 1.1222(2) 0.0280(6) Uani 1 1 d . . . H32A H 0.7326 0.2121 1.0973 0.042 Uiso 1 1 calc R . . H32B H 0.7609 0.0923 1.1856 0.042 Uiso 1 1 calc R . . H32C H 0.6064 0.1538 1.1295 0.042 Uiso 1 1 calc R . . C42 C 0.6151(4) -0.1523(4) 1.0884(2) 0.0405(9) Uani 1 1 d . . . H42A H 0.5312 -0.1240 1.1024 0.061 Uiso 1 1 calc R . . H42B H 0.6863 -0.1900 1.1481 0.061 Uiso 1 1 calc R . . H42C H 0.5925 -0.2340 1.0388 0.061 Uiso 1 1 calc R . . C62 C 0.3424(2) -0.0240(3) 0.71673(17) 0.0150(5) Uani 1 1 d . . . N72 N 0.2479(2) 0.0753(3) 0.66067(15) 0.0148(4) Uani 1 1 d . . . C82 C 0.1739(3) 0.0338(3) 0.56841(19) 0.0177(5) Uani 1 1 d . . . H82 H 0.1075 0.1044 0.5284 0.021 Uiso 1 1 calc R . . C92 C 0.1912(3) -0.1072(3) 0.53017(19) 0.0188(5) Uani 1 1 d . . . H92 H 0.1375 -0.1332 0.4648 0.023 Uiso 1 1 calc R . . C102 C 0.2879(3) -0.2108(3) 0.5882(2) 0.0189(6) Uani 1 1 d . . . H102 H 0.3016 -0.3088 0.5632 0.023 Uiso 1 1 calc R . . C112 C 0.3647(3) -0.1692(3) 0.68347(19) 0.0171(5) Uani 1 1 d . . . H112 H 0.4310 -0.2384 0.7250 0.021 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01588(13) 0.01368(13) 0.01559(12) -0.00213(10) 0.00111(9) 0.00268(10) Cl1 0.0190(3) 0.0207(3) 0.0193(3) 0.0000(2) 0.0046(2) 0.0011(2) Cl2 0.0183(3) 0.0188(3) 0.0210(3) -0.0017(2) 0.0042(2) 0.0009(2) N11 0.0184(10) 0.0196(11) 0.0165(10) -0.0058(8) 0.0008(8) 0.0035(8) N21 0.0178(10) 0.0163(11) 0.0154(10) -0.0029(8) 0.0021(8) 0.0026(8) N31 0.0168(10) 0.0163(11) 0.0172(10) -0.0018(8) 0.0018(8) 0.0030(8) N41 0.0145(9) 0.0184(11) 0.0158(10) -0.0004(9) 0.0001(8) 0.0021(8) C51 0.0148(11) 0.0158(12) 0.0139(11) -0.0010(9) 0.0033(9) -0.0003(9) C11 0.0189(12) 0.0220(13) 0.0137(12) -0.0033(9) -0.0039(10) 0.0040(10) C21 0.0217(13) 0.0245(15) 0.0392(17) 0.0118(13) -0.0042(12) -0.0063(12) C31 0.046(2) 0.055(2) 0.0231(15) -0.0190(15) -0.0097(14) 0.0309(18) C41 0.0196(12) 0.0252(14) 0.0187(12) 0.0034(10) 0.0031(10) 0.0008(10) C61 0.0125(10) 0.0145(12) 0.0157(11) 0.0008(9) 0.0040(9) -0.0001(9) N71 0.0140(10) 0.0168(11) 0.0139(9) 0.0005(8) 0.0021(8) 0.0012(8) C81 0.0163(11) 0.0220(13) 0.0149(11) -0.0001(10) 0.0024(9) 0.0013(10) C91 0.0211(13) 0.0215(14) 0.0147(11) -0.0017(10) 0.0042(10) 0.0011(10) C101 0.0219(14) 0.0137(14) 0.0205(14) -0.0029(9) 0.0082(11) -0.0012(9) C111 0.0175(11) 0.0163(13) 0.0163(12) 0.0011(10) 0.0035(9) 0.0011(10) N12 0.0157(10) 0.0181(11) 0.0145(9) 0.0002(8) 0.0025(8) 0.0004(8) N22 0.0129(9) 0.0191(11) 0.0146(10) 0.0004(8) 0.0031(8) -0.0013(8) N32 0.0153(10) 0.0218(12) 0.0180(11) -0.0031(9) 0.0044(8) -0.0013(8) N42 0.0157(10) 0.0182(11) 0.0169(10) -0.0016(8) 0.0026(9) 0.0013(8) C52 0.0130(11) 0.0147(12) 0.0179(12) -0.0015(9) 0.0060(9) -0.0021(9) C12 0.0165(11) 0.0231(13) 0.0134(11) 0.0035(9) 0.0005(9) -0.0044(10) C22 0.0206(13) 0.0315(16) 0.0207(13) 0.0015(11) -0.0026(11) 0.0065(12) C32 0.0206(13) 0.0399(17) 0.0203(12) -0.0078(12) 0.0028(10) -0.0042(12) C42 0.049(2) 0.0401(19) 0.0222(14) 0.0137(13) -0.0010(13) -0.0220(16) C62 0.0135(11) 0.0161(12) 0.0148(11) -0.0003(9) 0.0043(9) -0.0011(9) N72 0.0164(10) 0.0128(10) 0.0159(10) -0.0017(8) 0.0066(8) -0.0005(8) C82 0.0168(11) 0.0178(13) 0.0156(11) 0.0033(10) 0.0019(9) 0.0004(10) C92 0.0199(12) 0.0219(14) 0.0145(12) -0.0004(10) 0.0059(10) -0.0021(10) C102 0.0214(14) 0.0181(14) 0.0171(13) -0.0022(10) 0.0066(11) -0.0007(9) C112 0.0167(12) 0.0164(13) 0.0188(12) 0.0012(10) 0.0069(10) 0.0031(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N71 1.993(2) . ? Cu1 N72 2.005(2) . ? Cu1 Cl2 2.3234(7) . ? Cu1 Cl1 2.3253(7) . ? Cu1 N41 2.422(2) . ? Cu1 N42 2.493(2) . ? N11 C51 1.327(3) . ? N11 N21 1.334(3) . ? N21 N31 1.320(3) . ? N21 C11 1.501(3) . ? N31 N41 1.320(3) . ? N41 C51 1.345(4) . ? C51 C61 1.477(3) . ? C11 C31 1.511(4) . ? C11 C41 1.517(4) . ? C11 C21 1.528(4) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C61 N71 1.358(3) . ? C61 C111 1.380(4) . ? N71 C81 1.337(3) . ? C81 C91 1.394(4) . ? C81 H81 0.9500 . ? C91 C101 1.391(4) . ? C91 H91 0.9500 . ? C101 C111 1.386(4) . ? C101 H101 0.9500 . ? C111 H111 0.9500 . ? N12 N22 1.323(3) . ? N12 C52 1.332(3) . ? N22 N32 1.328(3) . ? N22 C12 1.507(3) . ? N32 N42 1.322(3) . ? N42 C52 1.350(4) . ? C52 C62 1.464(3) . ? C12 C32 1.522(4) . ? C12 C22 1.520(4) . ? C12 C42 1.522(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C62 N72 1.340(3) . ? C62 C112 1.390(4) . ? N72 C82 1.347(3) . ? C82 C92 1.375(4) . ? C82 H82 0.9500 . ? C92 C102 1.386(4) . ? C92 H92 0.9500 . ? C102 C112 1.390(4) . ? C102 H102 0.9500 . ? C112 H112 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N71 Cu1 N72 179.87(11) . . ? N71 Cu1 Cl2 89.93(7) . . ? N72 Cu1 Cl2 89.94(6) . . ? N71 Cu1 Cl1 89.14(7) . . ? N72 Cu1 Cl1 90.99(7) . . ? Cl2 Cu1 Cl1 179.06(3) . . ? N71 Cu1 N41 77.72(8) . . ? N72 Cu1 N41 102.30(8) . . ? Cl2 Cu1 N41 88.01(6) . . ? Cl1 Cu1 N41 91.60(6) . . ? C51 N11 N21 101.7(2) . . ? N31 N21 N11 113.4(2) . . ? N31 N21 C11 122.6(2) . . ? N11 N21 C11 123.3(2) . . ? N41 N31 N21 106.4(2) . . ? N31 N41 C51 106.0(2) . . ? N31 N41 Cu1 150.55(18) . . ? C51 N41 Cu1 103.31(15) . . ? N11 C51 N41 112.6(2) . . ? N11 C51 C61 124.5(2) . . ? N41 C51 C61 123.0(2) . . ? N21 C11 C31 108.5(2) . . ? N21 C11 C41 108.0(2) . . ? C31 C11 C41 110.3(3) . . ? N21 C11 C21 106.2(2) . . ? C31 C11 C21 113.5(3) . . ? C41 C11 C21 110.2(2) . . ? C11 C21 H21A 109.5 . . ? C11 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C11 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C11 C31 H31A 109.5 . . ? C11 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C11 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C11 C41 H41A 109.5 . . ? C11 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C11 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? N71 C61 C111 122.4(2) . . ? N71 C61 C51 115.2(2) . . ? C111 C61 C51 122.4(2) . . ? C81 N71 C61 118.4(2) . . ? C81 N71 Cu1 120.89(18) . . ? C61 N71 Cu1 120.67(17) . . ? N71 C81 C91 122.6(2) . . ? N71 C81 H81 118.7 . . ? C91 C81 H81 118.7 . . ? C101 C91 C81 118.4(2) . . ? C101 C91 H91 120.8 . . ? C81 C91 H91 120.8 . . ? C111 C101 C91 119.4(2) . . ? C111 C101 H101 120.3 . . ? C91 C101 H101 120.3 . . ? C61 C111 C101 118.8(2) . . ? C61 C111 H111 120.6 . . ? C101 C111 H111 120.6 . . ? N22 N12 C52 101.5(2) . . ? N12 N22 N32 114.2(2) . . ? N12 N22 C12 121.2(2) . . ? N32 N22 C12 124.5(2) . . ? N42 N32 N22 105.7(2) . . ? N32 N42 C52 106.2(2) . . ? N12 C52 N42 112.4(2) . . ? N12 C52 C62 124.2(2) . . ? N42 C52 C62 123.4(2) . . ? N22 C12 C32 108.2(2) . . ? N22 C12 C22 107.8(2) . . ? C32 C12 C22 110.5(2) . . ? N22 C12 C42 106.4(2) . . ? C32 C12 C42 111.2(3) . . ? C22 C12 C42 112.4(3) . . ? C12 C22 H22A 109.5 . . ? C12 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C12 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C12 C32 H32A 109.5 . . ? C12 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C12 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C12 C42 H42A 109.5 . . ? C12 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C12 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? N72 C62 C112 122.2(2) . . ? N72 C62 C52 116.7(2) . . ? C112 C62 C52 121.1(2) . . ? C62 N72 C82 118.7(2) . . ? C62 N72 Cu1 121.40(17) . . ? C82 N72 Cu1 119.91(18) . . ? N72 C82 C92 122.4(2) . . ? N72 C82 H82 118.8 . . ? C92 C82 H82 118.8 . . ? C82 C92 C102 119.1(2) . . ? C82 C92 H92 120.4 . . ? C102 C92 H92 120.4 . . ? C92 C102 C112 119.0(2) . . ? C92 C102 H102 120.5 . . ? C112 C102 H102 120.5 . . ? C102 C112 C62 118.6(2) . . ? C102 C112 H112 120.7 . . ? C62 C112 H112 120.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C51 N11 N21 N31 0.6(3) . . . . ? C51 N11 N21 C11 171.2(2) . . . . ? N11 N21 N31 N41 -0.6(3) . . . . ? C11 N21 N31 N41 -171.2(2) . . . . ? N21 N31 N41 C51 0.3(3) . . . . ? N21 N31 N41 Cu1 174.2(3) . . . . ? N71 Cu1 N41 N31 -174.1(4) . . . . ? N72 Cu1 N41 N31 6.0(4) . . . . ? Cl2 Cu1 N41 N31 95.5(4) . . . . ? Cl1 Cu1 N41 N31 -85.3(4) . . . . ? N71 Cu1 N41 C51 -0.10(17) . . . . ? N72 Cu1 N41 C51 -179.97(17) . . . . ? Cl2 Cu1 N41 C51 -90.47(17) . . . . ? Cl1 Cu1 N41 C51 88.67(17) . . . . ? N21 N11 C51 N41 -0.4(3) . . . . ? N21 N11 C51 C61 -179.5(2) . . . . ? N31 N41 C51 N11 0.1(3) . . . . ? Cu1 N41 C51 N11 -176.88(19) . . . . ? N31 N41 C51 C61 179.2(2) . . . . ? Cu1 N41 C51 C61 2.3(3) . . . . ? N31 N21 C11 C31 -36.6(4) . . . . ? N11 N21 C11 C31 153.6(3) . . . . ? N31 N21 C11 C41 -156.2(2) . . . . ? N11 N21 C11 C41 34.1(4) . . . . ? N31 N21 C11 C21 85.7(3) . . . . ? N11 N21 C11 C21 -84.1(3) . . . . ? N11 C51 C61 N71 174.8(2) . . . . ? N41 C51 C61 N71 -4.2(4) . . . . ? N11 C51 C61 C111 -4.6(4) . . . . ? N41 C51 C61 C111 176.4(3) . . . . ? C111 C61 N71 C81 1.2(4) . . . . ? C51 C61 N71 C81 -178.2(2) . . . . ? C111 C61 N71 Cu1 -176.6(2) . . . . ? C51 C61 N71 Cu1 4.0(3) . . . . ? Cl2 Cu1 N71 C81 -91.9(2) . . . . ? Cl1 Cu1 N71 C81 88.3(2) . . . . ? N41 Cu1 N71 C81 -179.9(2) . . . . ? Cl2 Cu1 N71 C61 85.79(19) . . . . ? Cl1 Cu1 N71 C61 -94.01(19) . . . . ? N41 Cu1 N71 C61 -2.19(19) . . . . ? C61 N71 C81 C91 0.6(4) . . . . ? Cu1 N71 C81 C91 178.4(2) . . . . ? N71 C81 C91 C101 -1.9(4) . . . . ? C81 C91 C101 C111 1.5(4) . . . . ? N71 C61 C111 C101 -1.6(4) . . . . ? C51 C61 C111 C101 177.8(2) . . . . ? C91 C101 C111 C61 0.1(4) . . . . ? C52 N12 N22 N32 0.3(3) . . . . ? C52 N12 N22 C12 178.7(2) . . . . ? N12 N22 N32 N42 -0.5(3) . . . . ? C12 N22 N32 N42 -178.8(2) . . . . ? N22 N32 N42 C52 0.4(3) . . . . ? N22 N12 C52 N42 -0.1(3) . . . . ? N22 N12 C52 C62 -179.3(2) . . . . ? N32 N42 C52 N12 -0.2(3) . . . . ? N32 N42 C52 C62 179.1(2) . . . . ? N12 N22 C12 C32 175.5(2) . . . . ? N32 N22 C12 C32 -6.3(3) . . . . ? N12 N22 C12 C22 55.9(3) . . . . ? N32 N22 C12 C22 -125.9(3) . . . . ? N12 N22 C12 C42 -64.9(3) . . . . ? N32 N22 C12 C42 113.3(3) . . . . ? N12 C52 C62 N72 -177.3(2) . . . . ? N42 C52 C62 N72 3.5(4) . . . . ? N12 C52 C62 C112 3.4(4) . . . . ? N42 C52 C62 C112 -175.8(2) . . . . ? C112 C62 N72 C82 -1.2(4) . . . . ? C52 C62 N72 C82 179.6(2) . . . . ? C112 C62 N72 Cu1 178.72(19) . . . . ? C52 C62 N72 Cu1 -0.5(3) . . . . ? Cl2 Cu1 N72 C62 90.29(19) . . . . ? Cl1 Cu1 N72 C62 -89.91(19) . . . . ? N41 Cu1 N72 C62 178.24(19) . . . . ? Cl2 Cu1 N72 C82 -89.78(19) . . . . ? Cl1 Cu1 N72 C82 90.02(19) . . . . ? N41 Cu1 N72 C82 -1.8(2) . . . . ? C62 N72 C82 C92 0.6(4) . . . . ? Cu1 N72 C82 C92 -179.3(2) . . . . ? N72 C82 C92 C102 0.0(4) . . . . ? C82 C92 C102 C112 0.0(4) . . . . ? C92 C102 C112 C62 -0.6(4) . . . . ? N72 C62 C112 C102 1.2(4) . . . . ? C52 C62 C112 C102 -179.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C21 H21B Cl2 0.98 2.77 3.687(3) 156.0 2_464 C22 H22B Cl1 0.98 2.72 3.692(3) 171. 2_655 C92 H92 Cl1 0.95 2.76 3.682(3) 164.0 2_554 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.797 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.067 data_2 _database_code_depnum_ccdc_archive 'CCDC 904344' #TrackingRef '14435_web_deposit_cif_file_2_AlexanderLyakhov_1349292712.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H26 Cu N12 S2' _chemical_formula_sum 'C22 H26 Cu N12 S2' _chemical_formula_weight 586.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.2627(4) _cell_length_b 9.3012(4) _cell_length_c 15.2346(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.8770(10) _cell_angle_gamma 90.00 _cell_volume 1367.59(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8638 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 30.00 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 0.987 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7561 _exptl_absorpt_correction_T_max 0.8271 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11896 _diffrn_reflns_av_R_equivalents 0.0134 _diffrn_reflns_av_sigmaI/netI 0.0105 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2687 _reflns_number_gt 2538 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2010)' _computing_data_reduction 'SAINT (Bruker, 2010)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material ; SHELXL-97 (Sheldrick, 2008), PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.6134P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2687 _refine_ls_number_parameters 203 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0246 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0667 _refine_ls_wR_factor_gt 0.0655 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.0000 0.5000 0.02289(9) Uani 1 2 d S . . N1 N 0.29768(12) 0.30473(14) 0.67123(8) 0.0246(3) Uani 1 1 d . . . N2 N 0.33210(12) 0.20786(13) 0.73977(8) 0.0227(3) Uani 1 1 d D A . N3 N 0.26133(13) 0.08626(14) 0.71854(8) 0.0267(3) Uani 1 1 d . . . N4 N 0.17683(12) 0.10174(14) 0.63158(8) 0.0272(3) Uani 1 1 d . . . C5 C 0.20030(14) 0.23407(16) 0.60437(10) 0.0232(3) Uani 1 1 d . . . C1 C 0.43483(14) 0.23748(16) 0.83535(9) 0.0242(3) Uani 1 1 d DU . . C2A C 0.3512(10) 0.2918(12) 0.8932(6) 0.045(2) Uani 0.378(9) 1 d PDU A 1 H2A1 H 0.2821 0.2195 0.8938 0.067 Uiso 0.378(9) 1 calc PR A 1 H2A2 H 0.3043 0.3813 0.8660 0.067 Uiso 0.378(9) 1 calc PR A 1 H2A3 H 0.4131 0.3098 0.9571 0.067 Uiso 0.378(9) 1 calc PR A 1 C3A C 0.5313(6) 0.3686(8) 0.8262(3) 0.0326(15) Uani 0.378(9) 1 d PDU A 1 H3A1 H 0.6012 0.3884 0.8873 0.049 Uiso 0.378(9) 1 calc PR A 1 H3A2 H 0.4741 0.4544 0.8040 0.049 Uiso 0.378(9) 1 calc PR A 1 H3A3 H 0.5775 0.3430 0.7817 0.049 Uiso 0.378(9) 1 calc PR A 1 C4A C 0.5200(10) 0.1111(7) 0.8694(5) 0.055(3) Uani 0.378(9) 1 d PDU A 1 H4A1 H 0.5693 0.0868 0.8265 0.083 Uiso 0.378(9) 1 calc PR A 1 H4A2 H 0.4609 0.0303 0.8733 0.083 Uiso 0.378(9) 1 calc PR A 1 H4A3 H 0.5872 0.1310 0.9315 0.083 Uiso 0.378(9) 1 calc PR A 1 C2B C 0.3670(7) 0.3416(4) 0.8815(4) 0.0350(11) Uani 0.622(9) 1 d PDU A 2 H2B1 H 0.2788 0.3016 0.8817 0.052 Uiso 0.622(9) 1 calc PR A 2 H2B2 H 0.3500 0.4326 0.8470 0.052 Uiso 0.622(9) 1 calc PR A 2 H2B3 H 0.4279 0.3586 0.9458 0.052 Uiso 0.622(9) 1 calc PR A 2 C3B C 0.5656(3) 0.2841(7) 0.8225(2) 0.0428(12) Uani 0.622(9) 1 d PDU A 2 H3B1 H 0.6360 0.3025 0.8836 0.064 Uiso 0.622(9) 1 calc PR A 2 H3B2 H 0.5488 0.3722 0.7851 0.064 Uiso 0.622(9) 1 calc PR A 2 H3B3 H 0.5982 0.2083 0.7904 0.064 Uiso 0.622(9) 1 calc PR A 2 C4B C 0.4612(4) 0.0914(3) 0.8911(2) 0.0258(7) Uani 0.622(9) 1 d PDU A 2 H4B1 H 0.4967 0.0197 0.8578 0.039 Uiso 0.622(9) 1 calc PR A 2 H4B2 H 0.3741 0.0570 0.8967 0.039 Uiso 0.622(9) 1 calc PR A 2 H4B3 H 0.5293 0.1066 0.9535 0.039 Uiso 0.622(9) 1 calc PR A 2 C6 C 0.12495(14) 0.29084(16) 0.51059(10) 0.0241(3) Uani 1 1 d . . . N7 N 0.03056(12) 0.20035(14) 0.45370(8) 0.0244(3) Uani 1 1 d . . . C8 C -0.04274(15) 0.24557(17) 0.36712(10) 0.0287(3) Uani 1 1 d . . . H8 H -0.1098 0.1829 0.3269 0.034 Uiso 1 1 calc R . . C9 C -0.02409(17) 0.38008(18) 0.33446(11) 0.0337(3) Uani 1 1 d . . . H9 H -0.0775 0.4089 0.2729 0.040 Uiso 1 1 calc R . . C10 C 0.07325(19) 0.47205(18) 0.39259(12) 0.0355(4) Uani 1 1 d . . . H10 H 0.0883 0.5645 0.3714 0.043 Uiso 1 1 calc R . . C11 C 0.14879(16) 0.42707(17) 0.48262(11) 0.0308(3) Uani 1 1 d . . . H11 H 0.2155 0.4886 0.5242 0.037 Uiso 1 1 calc R . . S1S S -0.31053(4) 0.23477(5) 0.62288(3) 0.03311(11) Uani 1 1 d . . . C1S C -0.21074(15) 0.14567(15) 0.57842(9) 0.0240(3) Uani 1 1 d . . . N7S N -0.13913(13) 0.08235(14) 0.54753(9) 0.0293(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01982(14) 0.02625(15) 0.01951(14) 0.00226(9) 0.00267(10) -0.00076(9) N1 0.0219(6) 0.0309(6) 0.0186(6) 0.0003(5) 0.0038(5) 0.0005(5) N2 0.0182(6) 0.0301(6) 0.0175(6) -0.0015(5) 0.0030(5) 0.0024(5) N3 0.0239(6) 0.0301(6) 0.0210(6) -0.0001(5) 0.0010(5) 0.0009(5) N4 0.0238(6) 0.0308(7) 0.0211(6) 0.0018(5) -0.0001(5) 0.0010(5) C5 0.0191(6) 0.0288(7) 0.0199(7) -0.0010(6) 0.0042(5) 0.0015(5) C1 0.0211(7) 0.0334(8) 0.0150(6) -0.0020(6) 0.0020(5) -0.0006(6) C2A 0.038(3) 0.073(6) 0.027(3) -0.012(4) 0.014(3) -0.007(4) C3A 0.026(2) 0.047(4) 0.019(2) -0.001(2) 0.0008(17) -0.016(2) C4A 0.064(5) 0.036(3) 0.035(3) -0.008(2) -0.024(3) 0.015(3) C2B 0.053(3) 0.0259(19) 0.0218(17) -0.0008(14) 0.0064(15) 0.0112(18) C3B 0.0266(15) 0.075(3) 0.0212(13) 0.0049(16) 0.0008(11) -0.0195(18) C4B 0.0266(15) 0.0274(13) 0.0188(13) 0.0001(10) 0.0019(11) 0.0077(11) C6 0.0190(6) 0.0306(7) 0.0202(7) -0.0001(6) 0.0033(5) 0.0009(6) N7 0.0199(6) 0.0300(6) 0.0202(6) 0.0017(5) 0.0029(5) -0.0003(5) C8 0.0247(7) 0.0348(8) 0.0211(7) 0.0021(6) 0.0006(6) -0.0021(6) C9 0.0334(8) 0.0375(8) 0.0227(7) 0.0070(7) -0.0003(6) -0.0002(7) C10 0.0398(9) 0.0312(8) 0.0294(8) 0.0066(7) 0.0040(7) -0.0039(7) C11 0.0295(8) 0.0323(8) 0.0256(7) 0.0000(6) 0.0030(6) -0.0046(6) S1S 0.0362(2) 0.0362(2) 0.0247(2) -0.00140(15) 0.00737(16) 0.00686(16) C1S 0.0248(7) 0.0244(7) 0.0172(6) 0.0033(5) -0.0002(5) -0.0039(6) N7S 0.0271(6) 0.0319(7) 0.0270(6) 0.0026(5) 0.0069(5) -0.0001(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N7S 1.9628(13) 3_556 ? Cu1 N7S 1.9629(13) . ? Cu1 N7 2.0540(12) 3_556 ? Cu1 N7 2.0540(12) . ? Cu1 N4 2.3944(12) . ? Cu1 N4 2.3945(12) 3_556 ? N1 C5 1.3326(18) . ? N1 N2 1.3327(17) . ? N2 N3 1.3235(18) . ? N2 C1 1.5045(17) . ? N3 N4 1.3216(17) . ? N4 C5 1.3464(19) . ? C5 C6 1.4720(19) . ? C1 C4A 1.451(5) . ? C1 C3B 1.485(3) . ? C1 C2B 1.499(5) . ? C1 C2A 1.510(8) . ? C1 C4B 1.576(3) . ? C1 C3A 1.607(5) . ? C2A H2A1 0.9800 . ? C2A H2A2 0.9800 . ? C2A H2A3 0.9800 . ? C3A H3A1 0.9800 . ? C3A H3A2 0.9800 . ? C3A H3A3 0.9800 . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C4A H4A3 0.9800 . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? C3B H3B1 0.9800 . ? C3B H3B2 0.9800 . ? C3B H3B3 0.9800 . ? C4B H4B1 0.9800 . ? C4B H4B2 0.9800 . ? C4B H4B3 0.9800 . ? C6 N7 1.3517(19) . ? C6 C11 1.385(2) . ? N7 C8 1.3445(19) . ? C8 C9 1.384(2) . ? C8 H8 0.9500 . ? C9 C10 1.383(2) . ? C9 H9 0.9500 . ? C10 C11 1.391(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? S1S C1S 1.6329(16) . ? C1S N7S 1.159(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7S Cu1 N7S 180.0 3_556 . ? N7S Cu1 N7 89.30(5) 3_556 3_556 ? N7S Cu1 N7 90.70(5) . 3_556 ? N7S Cu1 N7 90.70(5) 3_556 . ? N7S Cu1 N7 89.30(5) . . ? N7 Cu1 N7 180.0 3_556 . ? N7S Cu1 N4 91.36(5) 3_556 . ? N7S Cu1 N4 88.64(5) . . ? N7 Cu1 N4 103.40(4) 3_556 . ? N7 Cu1 N4 76.60(4) . . ? N7S Cu1 N4 88.64(5) 3_556 3_556 ? N7S Cu1 N4 91.36(5) . 3_556 ? N7 Cu1 N4 76.60(5) 3_556 3_556 ? N7 Cu1 N4 103.40(4) . 3_556 ? N4 Cu1 N4 180.0 . 3_556 ? C5 N1 N2 101.28(12) . . ? N3 N2 N1 114.14(11) . . ? N3 N2 C1 122.60(12) . . ? N1 N2 C1 123.12(12) . . ? N4 N3 N2 105.69(12) . . ? N3 N4 C5 106.45(12) . . ? N3 N4 Cu1 148.04(10) . . ? C5 N4 Cu1 105.52(9) . . ? N1 C5 N4 112.44(12) . . ? N1 C5 C6 125.09(13) . . ? N4 C5 C6 122.47(13) . . ? C4A C1 C3B 79.8(4) . . ? C4A C1 C2B 132.4(4) . . ? C3B C1 C2B 117.2(3) . . ? C4A C1 N2 109.7(2) . . ? C3B C1 N2 107.04(15) . . ? C2B C1 N2 106.7(3) . . ? C4A C1 C2A 117.1(5) . . ? C3B C1 C2A 134.2(4) . . ? N2 C1 C2A 106.0(4) . . ? C3B C1 C4B 109.0(2) . . ? C2B C1 C4B 109.0(2) . . ? N2 C1 C4B 107.41(15) . . ? C2A C1 C4B 90.1(4) . . ? C4A C1 C3A 109.4(4) . . ? C2B C1 C3A 87.0(3) . . ? N2 C1 C3A 107.74(19) . . ? C2A C1 C3A 106.6(4) . . ? C4B C1 C3A 134.7(3) . . ? C1 C2A H2A1 109.5 . . ? C1 C2A H2A2 109.5 . . ? C1 C2A H2A3 109.5 . . ? C1 C3A H3A1 109.5 . . ? C1 C3A H3A2 109.5 . . ? C1 C3A H3A3 109.5 . . ? C1 C4A H4A1 109.5 . . ? C1 C4A H4A2 109.5 . . ? C1 C4A H4A3 109.5 . . ? C1 C2B H2B1 109.5 . . ? C1 C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? C1 C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? C1 C3B H3B1 109.5 . . ? C1 C3B H3B2 109.5 . . ? H3B1 C3B H3B2 109.5 . . ? C1 C3B H3B3 109.5 . . ? H3B1 C3B H3B3 109.5 . . ? H3B2 C3B H3B3 109.5 . . ? C1 C4B H4B1 109.5 . . ? C1 C4B H4B2 109.5 . . ? H4B1 C4B H4B2 109.5 . . ? C1 C4B H4B3 109.5 . . ? H4B1 C4B H4B3 109.5 . . ? H4B2 C4B H4B3 109.5 . . ? N7 C6 C11 122.38(13) . . ? N7 C6 C5 115.11(13) . . ? C11 C6 C5 122.51(13) . . ? C8 N7 C6 118.31(13) . . ? C8 N7 Cu1 121.39(10) . . ? C6 N7 Cu1 120.30(10) . . ? N7 C8 C9 122.41(14) . . ? N7 C8 H8 118.8 . . ? C9 C8 H8 118.8 . . ? C10 C9 C8 119.15(14) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 118.99(15) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C6 C11 C10 118.76(14) . . ? C6 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? N7S C1S S1S 179.48(14) . . ? C1S N7S Cu1 171.56(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 N2 N3 -0.65(15) . . . . ? C5 N1 N2 C1 -176.40(12) . . . . ? N1 N2 N3 N4 0.70(16) . . . . ? C1 N2 N3 N4 176.48(12) . . . . ? N2 N3 N4 C5 -0.42(15) . . . . ? N2 N3 N4 Cu1 179.57(14) . . . . ? N7S Cu1 N4 N3 -89.51(19) 3_556 . . . ? N7S Cu1 N4 N3 90.49(19) . . . . ? N7 Cu1 N4 N3 0.10(19) 3_556 . . . ? N7 Cu1 N4 N3 -179.90(19) . . . . ? N7S Cu1 N4 C5 90.48(10) 3_556 . . . ? N7S Cu1 N4 C5 -89.52(10) . . . . ? N7 Cu1 N4 C5 -179.92(9) 3_556 . . . ? N7 Cu1 N4 C5 0.08(9) . . . . ? N2 N1 C5 N4 0.36(15) . . . . ? N2 N1 C5 C6 -179.57(13) . . . . ? N3 N4 C5 N1 0.04(16) . . . . ? Cu1 N4 C5 N1 -179.96(9) . . . . ? N3 N4 C5 C6 179.97(13) . . . . ? Cu1 N4 C5 C6 -0.03(16) . . . . ? N3 N2 C1 C4A 43.9(6) . . . . ? N1 N2 C1 C4A -140.8(6) . . . . ? N3 N2 C1 C3B 128.8(3) . . . . ? N1 N2 C1 C3B -55.8(3) . . . . ? N3 N2 C1 C2B -104.9(2) . . . . ? N1 N2 C1 C2B 70.5(3) . . . . ? N3 N2 C1 C2A -83.4(5) . . . . ? N1 N2 C1 C2A 92.0(5) . . . . ? N3 N2 C1 C4B 11.9(2) . . . . ? N1 N2 C1 C4B -172.71(17) . . . . ? N3 N2 C1 C3A 162.8(3) . . . . ? N1 N2 C1 C3A -21.8(4) . . . . ? N1 C5 C6 N7 179.84(13) . . . . ? N4 C5 C6 N7 -0.1(2) . . . . ? N1 C5 C6 C11 -0.2(2) . . . . ? N4 C5 C6 C11 179.84(14) . . . . ? C11 C6 N7 C8 -0.3(2) . . . . ? C5 C6 N7 C8 179.60(13) . . . . ? C11 C6 N7 Cu1 -179.75(11) . . . . ? C5 C6 N7 Cu1 0.18(17) . . . . ? N7S Cu1 N7 C8 89.22(12) 3_556 . . . ? N7S Cu1 N7 C8 -90.79(12) . . . . ? N4 Cu1 N7 C8 -179.55(12) . . . . ? N4 Cu1 N7 C8 0.45(12) 3_556 . . . ? N7S Cu1 N7 C6 -91.38(11) 3_556 . . . ? N7S Cu1 N7 C6 88.62(11) . . . . ? N4 Cu1 N7 C6 -0.14(10) . . . . ? N4 Cu1 N7 C6 179.86(10) 3_556 . . . ? C6 N7 C8 C9 0.5(2) . . . . ? Cu1 N7 C8 C9 179.91(12) . . . . ? N7 C8 C9 C10 0.0(3) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? N7 C6 C11 C10 -0.3(2) . . . . ? C5 C6 C11 C10 179.79(15) . . . . ? C9 C10 C11 C6 0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.301 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.042 data_3 _database_code_depnum_ccdc_archive 'CCDC 904345' #TrackingRef '14436_web_deposit_cif_file_3_AlexanderLyakhov_1349292712.3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 Cu N10 O, 2(Cl O4)' _chemical_formula_sum 'C20 H28 Cl2 Cu N10 O9' _chemical_formula_weight 686.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.510(2) _cell_length_b 6.9403(6) _cell_length_c 15.2164(13) _cell_angle_alpha 90.00 _cell_angle_beta 95.384(2) _cell_angle_gamma 90.00 _cell_volume 2787.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2873 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 28.57 _exptl_crystal_description lamina _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1412 _exptl_absorpt_coefficient_mu 1.044 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8184 _exptl_absorpt_correction_T_max 0.9794 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13549 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3191 _reflns_number_gt 2376 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2010)' _computing_data_reduction 'SAINT (Bruker, 2010)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material ; SHELXL-97 (Sheldrick, 2008), PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+2.5447P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3191 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0851 _refine_ls_wR_factor_gt 0.0764 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.22839(6) 0.2500 0.01147(11) Uani 1 2 d S . . Cl1 Cl 0.62838(2) 0.71978(8) 0.31619(4) 0.01707(14) Uani 1 1 d . . . O1 O 0.63367(9) 0.9019(3) 0.35940(13) 0.0408(6) Uani 1 1 d . . . O2 O 0.57556(6) 0.6587(3) 0.31226(13) 0.0277(4) Uani 1 1 d . . . O3 O 0.65929(6) 0.5780(2) 0.36436(11) 0.0234(4) Uani 1 1 d . . . O4 O 0.64229(7) 0.7352(3) 0.22734(11) 0.0316(5) Uani 1 1 d . . . N1 N 0.60424(7) 0.2379(3) 0.07333(12) 0.0136(4) Uani 1 1 d . . . N2 N 0.63638(7) 0.2354(3) 0.14654(12) 0.0127(4) Uani 1 1 d . . . C1 C 0.69296(8) 0.2267(3) 0.14255(15) 0.0140(5) Uani 1 1 d . . . C2 C 0.70768(9) 0.4084(3) 0.09440(15) 0.0180(5) Uani 1 1 d . . . H2A H 0.6902 0.4098 0.0347 0.027 Uiso 1 1 calc R . . H2B H 0.7444 0.4097 0.0909 0.027 Uiso 1 1 calc R . . H2C H 0.6978 0.5224 0.1268 0.027 Uiso 1 1 calc R . . C3 C 0.70369(9) 0.0451(3) 0.09088(16) 0.0190(5) Uani 1 1 d . . . H3A H 0.6917 -0.0680 0.1214 0.028 Uiso 1 1 calc R . . H3B H 0.7402 0.0339 0.0866 0.028 Uiso 1 1 calc R . . H3C H 0.6860 0.0529 0.0315 0.028 Uiso 1 1 calc R . . C4 C 0.71732(8) 0.2191(3) 0.23698(14) 0.0156(5) Uani 1 1 d . . . H4A H 0.7083 0.3353 0.2686 0.023 Uiso 1 1 calc R . . H4B H 0.7542 0.2120 0.2367 0.023 Uiso 1 1 calc R . . H4C H 0.7051 0.1050 0.2666 0.023 Uiso 1 1 calc R . . N3 N 0.61494(7) 0.2392(3) 0.22086(12) 0.0145(4) Uani 1 1 d . . . N4 N 0.56556(7) 0.2448(3) 0.19617(12) 0.0135(4) Uani 1 1 d . . . C5 C 0.56012(8) 0.2438(3) 0.10722(14) 0.0120(4) Uani 1 1 d . . . C6 C 0.50884(8) 0.2497(3) 0.06234(14) 0.0120(4) Uani 1 1 d . . . N7 N 0.47295(7) 0.2520(3) 0.12061(12) 0.0122(4) Uani 1 1 d . . . C8 C 0.42415(8) 0.2618(3) 0.08762(15) 0.0146(5) Uani 1 1 d . . . H8 H 0.3984 0.2641 0.1271 0.018 Uiso 1 1 calc R . . C9 C 0.41042(9) 0.2688(3) -0.00266(15) 0.0159(5) Uani 1 1 d . . . H9 H 0.3757 0.2766 -0.0243 0.019 Uiso 1 1 calc R . . C10 C 0.44738(9) 0.2643(3) -0.06120(16) 0.0168(5) Uani 1 1 d . . . H10 H 0.4384 0.2681 -0.1231 0.020 Uiso 1 1 calc R . . C11 C 0.49816(9) 0.2541(3) -0.02743(15) 0.0163(5) Uani 1 1 d . . . H11 H 0.5245 0.2503 -0.0656 0.020 Uiso 1 1 calc R . . O1W O 0.5000 -0.0872(4) 0.2500 0.0211(6) Uani 1 2 d S . . H1W H 0.5239(11) -0.157(5) 0.265(2) 0.048(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0074(2) 0.0188(2) 0.00827(19) 0.000 0.00104(14) 0.000 Cl1 0.0162(3) 0.0197(3) 0.0158(3) 0.0014(2) 0.0038(2) 0.0006(2) O1 0.0690(16) 0.0186(10) 0.0347(12) -0.0032(9) 0.0053(11) -0.0010(10) O2 0.0115(9) 0.0314(10) 0.0410(12) 0.0144(9) 0.0073(8) 0.0038(7) O3 0.0176(9) 0.0269(10) 0.0243(10) 0.0022(7) -0.0046(8) 0.0037(7) O4 0.0213(10) 0.0595(13) 0.0148(9) 0.0044(9) 0.0054(8) -0.0014(9) N1 0.0087(9) 0.0208(10) 0.0110(9) -0.0003(8) -0.0010(7) -0.0003(8) N2 0.0091(9) 0.0173(10) 0.0117(9) 0.0009(8) 0.0014(7) -0.0006(7) C1 0.0053(10) 0.0215(12) 0.0153(11) 0.0009(9) 0.0024(9) -0.0005(9) C2 0.0130(13) 0.0251(13) 0.0161(13) 0.0035(10) 0.0018(10) -0.0030(9) C3 0.0111(12) 0.0270(13) 0.0192(13) -0.0031(10) 0.0027(10) 0.0013(10) C4 0.0087(11) 0.0255(12) 0.0127(11) 0.0006(9) 0.0016(9) -0.0001(9) N3 0.0095(10) 0.0217(10) 0.0128(9) 0.0010(8) 0.0039(7) -0.0013(8) N4 0.0092(9) 0.0190(10) 0.0121(9) 0.0007(8) 0.0006(7) -0.0002(8) C5 0.0106(11) 0.0130(11) 0.0125(10) 0.0006(9) 0.0014(8) -0.0005(8) C6 0.0098(11) 0.0130(11) 0.0133(11) -0.0002(9) 0.0007(8) 0.0015(8) N7 0.0096(9) 0.0156(10) 0.0114(9) -0.0006(8) 0.0013(7) 0.0006(7) C8 0.0107(11) 0.0156(11) 0.0176(11) -0.0009(9) 0.0020(9) 0.0005(9) C9 0.0098(11) 0.0193(12) 0.0177(12) -0.0008(9) -0.0023(9) 0.0007(9) C10 0.0183(12) 0.0188(12) 0.0129(11) 0.0008(10) -0.0009(9) 0.0009(10) C11 0.0159(12) 0.0213(12) 0.0117(11) -0.0005(9) 0.0022(9) 0.0011(10) O1W 0.0155(14) 0.0195(13) 0.0269(15) 0.000 -0.0050(12) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.9928(19) . ? Cu1 N4 1.9929(19) 2_655 ? Cu1 N7 2.0377(18) 2_655 ? Cu1 N7 2.0377(18) . ? Cu1 O1W 2.190(3) . ? Cl1 O1 1.4255(19) . ? Cl1 O4 1.4383(18) . ? Cl1 O3 1.4366(17) . ? Cl1 O2 1.4589(18) . ? N1 C5 1.322(3) . ? N1 N2 1.338(3) . ? N2 N3 1.313(2) . ? N2 C1 1.508(3) . ? C1 C4 1.520(3) . ? C1 C3 1.526(3) . ? C1 C2 1.528(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? N3 N4 1.328(3) . ? N4 C5 1.348(3) . ? C5 C6 1.463(3) . ? C6 N7 1.360(3) . ? C6 C11 1.369(3) . ? N7 C8 1.345(3) . ? C8 C9 1.389(3) . ? C8 H8 0.9500 . ? C9 C10 1.385(3) . ? C9 H9 0.9500 . ? C10 C11 1.397(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? O1W H1W 0.82(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N4 173.46(11) . 2_655 ? N4 Cu1 N7 98.70(7) . 2_655 ? N4 Cu1 N7 80.77(7) 2_655 2_655 ? N4 Cu1 N7 80.78(7) . . ? N4 Cu1 N7 98.69(7) 2_655 . ? N7 Cu1 N7 170.79(10) 2_655 . ? N4 Cu1 O1W 93.27(5) . . ? N4 Cu1 O1W 93.27(5) 2_655 . ? N7 Cu1 O1W 94.61(5) 2_655 . ? N7 Cu1 O1W 94.61(5) . . ? O1 Cl1 O4 110.17(12) . . ? O1 Cl1 O3 110.19(12) . . ? O4 Cl1 O3 110.27(11) . . ? O1 Cl1 O2 109.22(13) . . ? O4 Cl1 O2 108.23(11) . . ? O3 Cl1 O2 108.73(10) . . ? C5 N1 N2 101.14(17) . . ? N3 N2 N1 115.08(18) . . ? N3 N2 C1 123.24(18) . . ? N1 N2 C1 121.68(17) . . ? N2 C1 C4 107.41(17) . . ? N2 C1 C3 106.74(18) . . ? C4 C1 C3 112.04(19) . . ? N2 C1 C2 106.61(18) . . ? C4 C1 C2 112.16(19) . . ? C3 C1 C2 111.49(19) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 N3 N4 104.59(17) . . ? N3 N4 C5 107.08(18) . . ? N3 N4 Cu1 139.16(15) . . ? C5 N4 Cu1 113.40(15) . . ? N1 C5 N4 112.12(19) . . ? N1 C5 C6 129.5(2) . . ? N4 C5 C6 118.4(2) . . ? N7 C6 C11 123.9(2) . . ? N7 C6 C5 111.85(19) . . ? C11 C6 C5 124.2(2) . . ? C8 N7 C6 117.68(19) . . ? C8 N7 Cu1 127.14(15) . . ? C6 N7 Cu1 115.13(14) . . ? N7 C8 C9 121.7(2) . . ? N7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C10 C9 C8 120.0(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 118.7(2) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C6 C11 C10 118.0(2) . . ? C6 C11 H11 121.0 . . ? C10 C11 H11 121.0 . . ? Cu1 O1W H1W 127(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 N2 N3 0.0(2) . . . . ? C5 N1 N2 C1 179.40(18) . . . . ? N3 N2 C1 C4 1.2(3) . . . . ? N1 N2 C1 C4 -178.10(19) . . . . ? N3 N2 C1 C3 121.5(2) . . . . ? N1 N2 C1 C3 -57.8(2) . . . . ? N3 N2 C1 C2 -119.2(2) . . . . ? N1 N2 C1 C2 61.5(2) . . . . ? N1 N2 N3 N4 -0.1(2) . . . . ? C1 N2 N3 N4 -179.43(18) . . . . ? N2 N3 N4 C5 0.1(2) . . . . ? N2 N3 N4 Cu1 172.30(17) . . . . ? N7 Cu1 N4 N3 11.5(2) 2_655 . . . ? N7 Cu1 N4 N3 -177.8(2) . . . . ? O1W Cu1 N4 N3 -83.6(2) . . . . ? N7 Cu1 N4 C5 -176.57(15) 2_655 . . . ? N7 Cu1 N4 C5 -5.88(15) . . . . ? O1W Cu1 N4 C5 88.26(14) . . . . ? N2 N1 C5 N4 0.0(2) . . . . ? N2 N1 C5 C6 179.8(2) . . . . ? N3 N4 C5 N1 -0.1(2) . . . . ? Cu1 N4 C5 N1 -174.53(14) . . . . ? N3 N4 C5 C6 -179.85(18) . . . . ? Cu1 N4 C5 C6 5.7(2) . . . . ? N1 C5 C6 N7 179.1(2) . . . . ? N4 C5 C6 N7 -1.1(3) . . . . ? N1 C5 C6 C11 -1.4(4) . . . . ? N4 C5 C6 C11 178.4(2) . . . . ? C11 C6 N7 C8 -1.0(3) . . . . ? C5 C6 N7 C8 178.53(18) . . . . ? C11 C6 N7 Cu1 176.57(17) . . . . ? C5 C6 N7 Cu1 -3.9(2) . . . . ? N4 Cu1 N7 C8 -177.26(19) . . . . ? N4 Cu1 N7 C8 -3.86(19) 2_655 . . . ? O1W Cu1 N7 C8 90.17(17) . . . . ? N4 Cu1 N7 C6 5.47(15) . . . . ? N4 Cu1 N7 C6 178.88(15) 2_655 . . . ? O1W Cu1 N7 C6 -87.10(14) . . . . ? C6 N7 C8 C9 0.2(3) . . . . ? Cu1 N7 C8 C9 -176.97(16) . . . . ? N7 C8 C9 C10 0.4(3) . . . . ? C8 C9 C10 C11 -0.4(3) . . . . ? N7 C6 C11 C10 1.0(3) . . . . ? C5 C6 C11 C10 -178.5(2) . . . . ? C9 C10 C11 C6 -0.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1W O2 0.82(3) 1.96(3) 2.769(2) 173(3) 1_545 C3 H3A O4 0.98 2.56 3.496(3) 159. 1_545 C8 H8 N3 0.95 2.38 3.187(3) 143. 2_655 C10 H10 O4 0.95 2.54 3.304(3) 138. 5_665 C11 H11 O2 0.95 2.48 3.386(3) 159. 6_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.406 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.071 data_4 _database_code_depnum_ccdc_archive 'CCDC 904346' #TrackingRef '14437_web_deposit_cif_file_4_AlexanderLyakhov_1349292712.4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H44 Cu2 Mn N10 O12' _chemical_formula_sum 'C32 H44 Cu2 Mn N10 O12' _chemical_formula_weight 942.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5655(4) _cell_length_b 9.9404(5) _cell_length_c 12.7777(7) _cell_angle_alpha 81.761(2) _cell_angle_beta 75.090(2) _cell_angle_gamma 70.822(2) _cell_volume 990.91(9) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9258 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 30.46 _exptl_crystal_description lamina _exptl_crystal_colour blue _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 485 _exptl_absorpt_coefficient_mu 1.449 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7703 _exptl_absorpt_correction_T_max 0.9311 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19035 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4525 _reflns_number_gt 4027 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2010)' _computing_data_reduction 'SAINT (Bruker, 2010)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material ; SHELXL-97 (Sheldrick, 2008), PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+0.5980P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4525 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0290 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0605 _refine_ls_wR_factor_gt 0.0571 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.61374(2) 0.72937(2) 0.689356(14) 0.01142(6) Uani 1 1 d . . . Mn1 Mn 0.5000 1.0000 0.5000 0.01108(8) Uani 1 2 d S . . N1 N 0.70473(16) 0.52411(14) 0.81188(10) 0.0130(3) Uani 1 1 d . . . N2 N 0.71080(16) 0.39256(14) 0.85413(10) 0.0131(3) Uani 1 1 d . . . N3 N 0.83756(17) 0.33194(15) 0.90365(11) 0.0168(3) Uani 1 1 d . . . N4 N 0.91959(17) 0.42664(15) 0.89434(11) 0.0166(3) Uani 1 1 d . . . C5 C 0.83613(19) 0.54216(17) 0.83858(12) 0.0131(3) Uani 1 1 d . . . C1 C 0.5857(2) 0.32156(17) 0.84448(12) 0.0144(3) Uani 1 1 d . . . C2 C 0.4096(2) 0.42377(19) 0.88547(14) 0.0200(3) Uani 1 1 d . . . H2A H 0.3976 0.4442 0.9604 0.030 Uiso 1 1 calc R . . H2B H 0.3236 0.3800 0.8829 0.030 Uiso 1 1 calc R . . H2C H 0.3944 0.5128 0.8395 0.030 Uiso 1 1 calc R . . C3 C 0.6172(2) 0.18156(19) 0.91424(14) 0.0216(4) Uani 1 1 d . . . H3A H 0.7338 0.1210 0.8884 0.032 Uiso 1 1 calc R . . H3B H 0.5377 0.1322 0.9091 0.032 Uiso 1 1 calc R . . H3C H 0.6005 0.2015 0.9900 0.032 Uiso 1 1 calc R . . C4 C 0.6153(2) 0.29819(19) 0.72486(13) 0.0189(3) Uani 1 1 d . . . H4A H 0.5974 0.3904 0.6829 0.028 Uiso 1 1 calc R . . H4B H 0.5356 0.2515 0.7155 0.028 Uiso 1 1 calc R . . H4C H 0.7318 0.2375 0.6992 0.028 Uiso 1 1 calc R . . C6 C 0.88488(19) 0.67308(17) 0.80788(12) 0.0139(3) Uani 1 1 d . . . N7 N 0.80567(16) 0.76734(14) 0.73630(11) 0.0136(3) Uani 1 1 d . . . C8 C 0.8542(2) 0.88421(18) 0.70083(14) 0.0179(3) Uani 1 1 d . . . H8 H 0.7990 0.9514 0.6509 0.021 Uiso 1 1 calc R . . C9 C 0.9826(2) 0.91012(19) 0.73472(14) 0.0205(3) Uani 1 1 d . . . H9 H 1.0176 0.9919 0.7062 0.025 Uiso 1 1 calc R . . C10 C 1.0593(2) 0.81524(19) 0.81075(14) 0.0201(3) Uani 1 1 d . . . H10 H 1.1453 0.8324 0.8365 0.024 Uiso 1 1 calc R . . C11 C 1.0086(2) 0.69504(18) 0.84853(13) 0.0173(3) Uani 1 1 d . . . H11 H 1.0579 0.6290 0.9014 0.021 Uiso 1 1 calc R . . C12 C 0.2515(2) 0.65108(19) 0.55839(13) 0.0188(3) Uani 1 1 d . . . H12A H 0.1724 0.7176 0.5173 0.028 Uiso 1 1 calc R . . H12B H 0.1875 0.6203 0.6277 0.028 Uiso 1 1 calc R . . H12C H 0.3187 0.5677 0.5164 0.028 Uiso 1 1 calc R . . C13 C 0.36833(19) 0.72440(17) 0.57956(12) 0.0127(3) Uani 1 1 d . . . O1 O 0.43761(14) 0.67012(12) 0.65895(9) 0.0167(2) Uani 1 1 d . . . O2 O 0.39099(15) 0.82982(12) 0.51929(9) 0.0182(2) Uani 1 1 d . . . C14 C 0.9197(2) 0.66128(19) 0.38051(14) 0.0206(3) Uani 1 1 d . . . H14A H 0.8516 0.6374 0.3392 0.031 Uiso 1 1 calc R . . H14B H 1.0081 0.5747 0.3971 0.031 Uiso 1 1 calc R . . H14C H 0.9727 0.7312 0.3374 0.031 Uiso 1 1 calc R . . C15 C 0.80782(19) 0.72325(17) 0.48417(13) 0.0150(3) Uani 1 1 d . . . O3 O 0.75357(14) 0.85607(12) 0.48984(10) 0.0179(2) Uani 1 1 d . . . O4 O 0.77248(14) 0.63557(12) 0.56253(9) 0.0157(2) Uani 1 1 d . . . C16 C 0.2592(2) 1.07845(18) 0.84503(14) 0.0191(3) Uani 1 1 d . . . H16A H 0.2660 1.1756 0.8251 0.029 Uiso 1 1 calc R . . H16B H 0.2744 1.0504 0.9194 0.029 Uiso 1 1 calc R . . H16C H 0.1480 1.0752 0.8405 0.029 Uiso 1 1 calc R . . C17 C 0.39656(19) 0.97704(17) 0.76822(12) 0.0137(3) Uani 1 1 d . . . O5 O 0.44665(14) 0.84726(12) 0.80348(9) 0.0157(2) Uani 1 1 d . . . O6 O 0.45356(15) 1.02331(13) 0.67518(9) 0.0194(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01090(10) 0.01115(10) 0.01260(10) 0.00019(7) -0.00416(7) -0.00310(7) Mn1 0.01156(16) 0.00886(16) 0.01223(16) 0.00113(12) -0.00358(12) -0.00239(12) N1 0.0134(6) 0.0131(6) 0.0120(6) -0.0003(5) -0.0032(5) -0.0033(5) N2 0.0151(6) 0.0129(6) 0.0108(6) 0.0004(5) -0.0034(5) -0.0036(5) N3 0.0162(7) 0.0172(7) 0.0164(6) 0.0007(5) -0.0062(5) -0.0030(6) N4 0.0160(7) 0.0168(7) 0.0165(7) 0.0002(5) -0.0056(5) -0.0035(6) C5 0.0120(7) 0.0146(8) 0.0109(7) -0.0032(6) -0.0016(5) -0.0013(6) C1 0.0168(8) 0.0139(8) 0.0140(7) -0.0007(6) -0.0032(6) -0.0069(6) C2 0.0158(8) 0.0204(9) 0.0235(9) -0.0037(7) -0.0013(6) -0.0064(7) C3 0.0281(9) 0.0183(9) 0.0205(8) 0.0042(7) -0.0079(7) -0.0105(7) C4 0.0245(9) 0.0189(8) 0.0156(8) -0.0020(6) -0.0044(6) -0.0092(7) C6 0.0110(7) 0.0156(8) 0.0135(7) -0.0032(6) -0.0009(6) -0.0024(6) N7 0.0123(6) 0.0133(7) 0.0154(6) -0.0022(5) -0.0039(5) -0.0031(5) C8 0.0174(8) 0.0142(8) 0.0229(8) -0.0017(6) -0.0060(6) -0.0045(6) C9 0.0188(8) 0.0159(8) 0.0292(9) -0.0037(7) -0.0057(7) -0.0073(7) C10 0.0157(8) 0.0224(9) 0.0259(9) -0.0065(7) -0.0074(7) -0.0065(7) C11 0.0143(8) 0.0200(8) 0.0176(8) -0.0022(6) -0.0055(6) -0.0036(6) C12 0.0233(8) 0.0236(9) 0.0148(7) -0.0005(6) -0.0051(6) -0.0138(7) C13 0.0121(7) 0.0125(7) 0.0128(7) -0.0033(6) -0.0015(5) -0.0029(6) O1 0.0169(6) 0.0187(6) 0.0174(6) 0.0028(5) -0.0066(4) -0.0091(5) O2 0.0222(6) 0.0155(6) 0.0203(6) 0.0033(5) -0.0080(5) -0.0098(5) C14 0.0216(8) 0.0175(8) 0.0185(8) 0.0002(6) -0.0014(6) -0.0032(7) C15 0.0106(7) 0.0161(8) 0.0190(8) -0.0005(6) -0.0071(6) -0.0027(6) O3 0.0136(5) 0.0123(6) 0.0268(6) -0.0015(5) -0.0070(5) -0.0007(4) O4 0.0162(5) 0.0143(6) 0.0157(5) -0.0012(4) -0.0032(4) -0.0037(5) C16 0.0192(8) 0.0159(8) 0.0206(8) -0.0019(6) -0.0040(6) -0.0032(7) C17 0.0135(7) 0.0162(8) 0.0148(7) -0.0017(6) -0.0063(6) -0.0065(6) O5 0.0155(5) 0.0147(6) 0.0155(5) -0.0005(4) -0.0031(4) -0.0032(5) O6 0.0263(6) 0.0204(6) 0.0136(5) 0.0002(5) -0.0042(5) -0.0106(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9299(11) . ? Cu1 O4 1.9521(11) . ? Cu1 O5 1.9652(11) . ? Cu1 N7 2.0458(13) . ? Cu1 N1 2.4267(13) . ? Mn1 O2 2.1434(11) 2_676 ? Mn1 O2 2.1434(11) . ? Mn1 O3 2.1559(11) 2_676 ? Mn1 O3 2.1559(11) . ? Mn1 O6 2.2028(11) 2_676 ? Mn1 O6 2.2028(11) . ? N1 C5 1.328(2) . ? N1 N2 1.3310(18) . ? N2 N3 1.3254(19) . ? N2 C1 1.5003(19) . ? N3 N4 1.3241(19) . ? N4 C5 1.351(2) . ? C5 C6 1.466(2) . ? C1 C4 1.523(2) . ? C1 C2 1.524(2) . ? C1 C3 1.525(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C6 N7 1.353(2) . ? C6 C11 1.381(2) . ? N7 C8 1.341(2) . ? C8 C9 1.388(2) . ? C8 H8 0.9500 . ? C9 C10 1.387(2) . ? C9 H9 0.9500 . ? C10 C11 1.385(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.510(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O2 1.2468(19) . ? C13 O1 1.2708(19) . ? C14 C15 1.498(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O3 1.253(2) . ? C15 O4 1.2732(19) . ? C16 C17 1.508(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 O6 1.2471(19) . ? C17 O5 1.2730(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O4 89.87(5) . . ? O1 Cu1 O5 90.19(5) . . ? O4 Cu1 O5 172.13(5) . . ? O1 Cu1 N7 171.97(5) . . ? O4 Cu1 N7 90.96(5) . . ? O5 Cu1 N7 90.07(5) . . ? O1 Cu1 N1 95.22(5) . . ? O4 Cu1 N1 92.88(5) . . ? O5 Cu1 N1 94.95(4) . . ? N7 Cu1 N1 76.76(5) . . ? O2 Mn1 O2 180.00(5) 2_676 . ? O2 Mn1 O3 93.20(4) 2_676 2_676 ? O2 Mn1 O3 86.80(4) . 2_676 ? O2 Mn1 O3 86.80(4) 2_676 . ? O2 Mn1 O3 93.20(4) . . ? O3 Mn1 O3 179.999(1) 2_676 . ? O2 Mn1 O6 95.06(4) 2_676 2_676 ? O2 Mn1 O6 84.94(4) . 2_676 ? O3 Mn1 O6 94.02(4) 2_676 2_676 ? O3 Mn1 O6 85.98(4) . 2_676 ? O2 Mn1 O6 84.94(4) 2_676 . ? O2 Mn1 O6 95.06(4) . . ? O3 Mn1 O6 85.98(4) 2_676 . ? O3 Mn1 O6 94.02(4) . . ? O6 Mn1 O6 179.999(1) 2_676 . ? C5 N1 N2 101.80(12) . . ? C5 N1 Cu1 104.36(10) . . ? N2 N1 Cu1 152.39(10) . . ? N3 N2 N1 113.50(13) . . ? N3 N2 C1 124.21(13) . . ? N1 N2 C1 122.29(12) . . ? N4 N3 N2 106.35(13) . . ? N3 N4 C5 105.72(13) . . ? N1 C5 N4 112.64(14) . . ? N1 C5 C6 122.72(14) . . ? N4 C5 C6 124.63(14) . . ? N2 C1 C4 107.23(12) . . ? N2 C1 C2 106.76(13) . . ? C4 C1 C2 111.00(14) . . ? N2 C1 C3 107.56(13) . . ? C4 C1 C3 112.27(14) . . ? C2 C1 C3 111.70(13) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N7 C6 C11 122.74(15) . . ? N7 C6 C5 116.35(14) . . ? C11 C6 C5 120.89(14) . . ? C8 N7 C6 118.23(14) . . ? C8 N7 Cu1 122.59(11) . . ? C6 N7 Cu1 119.16(11) . . ? N7 C8 C9 122.10(16) . . ? N7 C8 H8 119.0 . . ? C9 C8 H8 119.0 . . ? C10 C9 C8 119.25(16) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C11 C10 C9 118.90(15) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C6 C11 C10 118.69(15) . . ? C6 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 O1 125.35(14) . . ? O2 C13 C12 119.11(14) . . ? O1 C13 C12 115.54(14) . . ? C13 O1 Cu1 122.78(10) . . ? C13 O2 Mn1 143.64(10) . . ? C15 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O3 C15 O4 123.49(15) . . ? O3 C15 C14 119.53(14) . . ? O4 C15 C14 116.98(14) . . ? C15 O3 Mn1 129.82(10) . . ? C15 O4 Cu1 113.05(10) . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O6 C17 O5 123.95(15) . . ? O6 C17 C16 119.20(14) . . ? O5 C17 C16 116.84(13) . . ? C17 O5 Cu1 110.99(10) . . ? C17 O6 Mn1 145.38(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 N1 C5 176.92(10) . . . . ? O4 Cu1 N1 C5 86.79(10) . . . . ? O5 Cu1 N1 C5 -92.43(10) . . . . ? N7 Cu1 N1 C5 -3.53(10) . . . . ? O1 Cu1 N1 N2 16.0(2) . . . . ? O4 Cu1 N1 N2 -74.1(2) . . . . ? O5 Cu1 N1 N2 106.7(2) . . . . ? N7 Cu1 N1 N2 -164.4(2) . . . . ? C5 N1 N2 N3 -0.20(16) . . . . ? Cu1 N1 N2 N3 160.91(17) . . . . ? C5 N1 N2 C1 -179.59(13) . . . . ? Cu1 N1 N2 C1 -18.5(3) . . . . ? N1 N2 N3 N4 0.08(17) . . . . ? C1 N2 N3 N4 179.45(13) . . . . ? N2 N3 N4 C5 0.08(16) . . . . ? N2 N1 C5 N4 0.25(16) . . . . ? Cu1 N1 C5 N4 -170.84(10) . . . . ? N2 N1 C5 C6 179.02(14) . . . . ? Cu1 N1 C5 C6 7.93(16) . . . . ? N3 N4 C5 N1 -0.22(17) . . . . ? N3 N4 C5 C6 -178.96(14) . . . . ? N3 N2 C1 C4 -113.05(16) . . . . ? N1 N2 C1 C4 66.27(17) . . . . ? N3 N2 C1 C2 127.92(15) . . . . ? N1 N2 C1 C2 -52.76(17) . . . . ? N3 N2 C1 C3 7.9(2) . . . . ? N1 N2 C1 C3 -172.78(13) . . . . ? N1 C5 C6 N7 -9.9(2) . . . . ? N4 C5 C6 N7 168.72(14) . . . . ? N1 C5 C6 C11 171.79(15) . . . . ? N4 C5 C6 C11 -9.6(2) . . . . ? C11 C6 N7 C8 2.4(2) . . . . ? C5 C6 N7 C8 -175.85(14) . . . . ? C11 C6 N7 Cu1 -176.08(12) . . . . ? C5 C6 N7 Cu1 5.66(18) . . . . ? O4 Cu1 N7 C8 87.64(13) . . . . ? O5 Cu1 N7 C8 -84.56(13) . . . . ? N1 Cu1 N7 C8 -179.64(13) . . . . ? O4 Cu1 N7 C6 -93.94(12) . . . . ? O5 Cu1 N7 C6 93.87(12) . . . . ? N1 Cu1 N7 C6 -1.21(11) . . . . ? C6 N7 C8 C9 0.4(2) . . . . ? Cu1 N7 C8 C9 178.84(13) . . . . ? N7 C8 C9 C10 -2.5(3) . . . . ? C8 C9 C10 C11 1.7(3) . . . . ? N7 C6 C11 C10 -3.1(2) . . . . ? C5 C6 C11 C10 175.12(15) . . . . ? C9 C10 C11 C6 0.9(2) . . . . ? O2 C13 O1 Cu1 -7.7(2) . . . . ? C12 C13 O1 Cu1 171.53(10) . . . . ? O4 Cu1 O1 C13 -71.65(12) . . . . ? O5 Cu1 O1 C13 100.48(12) . . . . ? N1 Cu1 O1 C13 -164.53(12) . . . . ? O1 C13 O2 Mn1 -10.3(3) . . . . ? C12 C13 O2 Mn1 170.47(13) . . . . ? O3 Mn1 O2 C13 -117.74(18) 2_676 . . . ? O3 Mn1 O2 C13 62.26(18) . . . . ? O6 Mn1 O2 C13 147.93(18) 2_676 . . . ? O6 Mn1 O2 C13 -32.07(18) . . . . ? O4 C15 O3 Mn1 -69.7(2) . . . . ? C14 C15 O3 Mn1 109.95(15) . . . . ? O2 Mn1 O3 C15 -172.42(14) 2_676 . . . ? O2 Mn1 O3 C15 7.59(14) . . . . ? O6 Mn1 O3 C15 -77.11(14) 2_676 . . . ? O6 Mn1 O3 C15 102.89(14) . . . . ? O3 C15 O4 Cu1 3.62(19) . . . . ? C14 C15 O4 Cu1 -176.05(11) . . . . ? O1 Cu1 O4 C15 107.49(10) . . . . ? N7 Cu1 O4 C15 -80.50(11) . . . . ? N1 Cu1 O4 C15 -157.29(10) . . . . ? O6 C17 O5 Cu1 -3.53(18) . . . . ? C16 C17 O5 Cu1 176.10(10) . . . . ? O1 Cu1 O5 C17 -97.69(10) . . . . ? N7 Cu1 O5 C17 90.34(10) . . . . ? N1 Cu1 O5 C17 167.05(10) . . . . ? O5 C17 O6 Mn1 55.6(3) . . . . ? C16 C17 O6 Mn1 -124.02(18) . . . . ? O2 Mn1 O6 C17 -178.5(2) 2_676 . . . ? O2 Mn1 O6 C17 1.5(2) . . . . ? O3 Mn1 O6 C17 87.9(2) 2_676 . . . ? O3 Mn1 O6 C17 -92.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C3 H3C O5 0.98 2.56 3.490(2) 158. 2_667 C8 H8 O3 0.95 2.55 3.108(2) 118. . C10 H10 O5 0.95 2.56 3.412(2) 150. 1_655 C14 H14B O4 0.98 2.40 3.384(2) 179. 2_766 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.378 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.057 data_5 _database_code_depnum_ccdc_archive 'CCDC 904347' #TrackingRef '14438_web_deposit_cif_file_5_AlexanderLyakhov_1349292712.5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H44 Cu2 Mn N10 O12, 2(C2 H6 O S)' _chemical_formula_sum 'C36 H56 Cu2 Mn N10 O14 S2' _chemical_formula_weight 1099.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.34040(10) _cell_length_b 8.63110(10) _cell_length_c 17.2045(2) _cell_angle_alpha 93.7780(10) _cell_angle_beta 93.0760(10) _cell_angle_gamma 98.7330(10) _cell_volume 1218.93(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9911 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 30.59 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 569 _exptl_absorpt_coefficient_mu 1.275 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5150 _exptl_absorpt_correction_T_max 0.7410 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22630 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0125 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5592 _reflns_number_gt 5303 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2010)' _computing_data_reduction 'SAINT (Bruker, 2010)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material ; SHELXL-97 (Sheldrick, 2008), PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.6371P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5592 _refine_ls_number_parameters 311 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0613 _refine_ls_wR_factor_gt 0.0603 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.912689(18) 0.901557(18) 0.685094(8) 0.01469(5) Uani 1 1 d . . . Mn1 Mn 1.0000 1.0000 0.5000 0.01202(6) Uani 1 2 d S . . N1 N 0.98632(14) 0.73102(13) 0.91156(6) 0.0176(2) Uani 1 1 d . . . N2 N 0.84077(14) 0.76519(13) 0.92736(6) 0.0165(2) Uani 1 1 d . . . N3 N 0.76724(14) 0.82787(13) 0.87008(6) 0.0186(2) Uani 1 1 d . . . N4 N 0.86699(14) 0.83461(13) 0.81305(6) 0.0178(2) Uani 1 1 d . . . C5 C 0.99854(16) 0.77565(14) 0.83906(7) 0.0159(2) Uani 1 1 d . . . C1 C 0.76803(17) 0.74261(16) 1.00441(7) 0.0196(3) Uani 1 1 d . . . C2 C 0.8420(2) 0.88306(19) 1.06001(8) 0.0301(3) Uani 1 1 d . . . H2A H 0.9605 0.8894 1.0643 0.045 Uiso 1 1 calc R . . H2B H 0.7994 0.8704 1.1116 0.045 Uiso 1 1 calc R . . H2C H 0.8137 0.9797 1.0399 0.045 Uiso 1 1 calc R . . C3 C 0.58441(18) 0.73401(18) 0.99109(8) 0.0248(3) Uani 1 1 d . . . H3A H 0.5598 0.8359 0.9762 0.037 Uiso 1 1 calc R . . H3B H 0.5323 0.7078 1.0393 0.037 Uiso 1 1 calc R . . H3C H 0.5432 0.6528 0.9493 0.037 Uiso 1 1 calc R . . C4 C 0.8090(2) 0.58933(18) 1.03301(8) 0.0265(3) Uani 1 1 d . . . H4A H 0.7659 0.5025 0.9944 0.040 Uiso 1 1 calc R . . H4B H 0.7602 0.5707 1.0828 0.040 Uiso 1 1 calc R . . H4C H 0.9273 0.5961 1.0403 0.040 Uiso 1 1 calc R . . C6 C 1.13677(15) 0.76494(14) 0.79089(7) 0.0159(2) Uani 1 1 d . . . N7 N 1.11606(13) 0.80461(12) 0.71672(6) 0.0158(2) Uani 1 1 d . . . C8 C 1.23802(16) 0.79619(15) 0.66952(8) 0.0188(3) Uani 1 1 d . . . H8 H 1.2241 0.8226 0.6171 0.023 Uiso 1 1 calc R . . C9 C 1.38385(16) 0.75035(16) 0.69447(8) 0.0204(3) Uani 1 1 d . . . H9 H 1.4681 0.7461 0.6597 0.025 Uiso 1 1 calc R . . C10 C 1.40439(17) 0.71088(16) 0.77082(9) 0.0219(3) Uani 1 1 d . . . H10 H 1.5031 0.6795 0.7893 0.026 Uiso 1 1 calc R . . C11 C 1.27856(17) 0.71794(16) 0.81971(8) 0.0202(3) Uani 1 1 d . . . H11 H 1.2894 0.6910 0.8722 0.024 Uiso 1 1 calc R . . C12 C 0.53578(16) 1.12536(17) 0.58867(8) 0.0230(3) Uani 1 1 d . . . H12A H 0.5415 1.1994 0.5477 0.035 Uiso 1 1 calc R . . H12B H 0.5198 1.1804 0.6386 0.035 Uiso 1 1 calc R . . H12C H 0.4445 1.0402 0.5755 0.035 Uiso 1 1 calc R . . C13 C 0.69232(15) 1.05761(15) 0.59502(7) 0.0160(2) Uani 1 1 d . . . O1 O 0.72398(12) 1.00081(12) 0.65914(6) 0.0236(2) Uani 1 1 d . . . O2 O 0.77823(11) 1.06167(12) 0.53806(6) 0.0215(2) Uani 1 1 d . . . C14 C 1.20507(19) 1.33470(17) 0.69199(9) 0.0276(3) Uani 1 1 d . . . H14A H 1.3081 1.3489 0.6666 0.041 Uiso 1 1 calc R . . H14B H 1.2267 1.3536 0.7486 0.041 Uiso 1 1 calc R . . H14C H 1.1368 1.4092 0.6733 0.041 Uiso 1 1 calc R . . C15 C 1.11850(15) 1.16945(15) 0.67282(7) 0.0168(2) Uani 1 1 d . . . O3 O 1.13329(11) 1.10095(11) 0.60807(5) 0.01933(19) Uani 1 1 d . . . O4 O 1.03243(12) 1.10762(11) 0.72492(6) 0.02067(19) Uani 1 1 d . . . C16 C 0.7707(2) 0.51806(19) 0.52596(10) 0.0355(4) Uani 1 1 d . . . H16A H 0.7516 0.5346 0.4706 0.053 Uiso 1 1 calc R . . H16B H 0.6670 0.4796 0.5477 0.053 Uiso 1 1 calc R . . H16C H 0.8442 0.4404 0.5312 0.053 Uiso 1 1 calc R . . C17 C 0.84627(17) 0.67116(15) 0.56957(8) 0.0193(3) Uani 1 1 d . . . O5 O 0.79961(12) 0.70012(12) 0.63758(6) 0.0223(2) Uani 1 1 d . . . O6 O 0.95167(12) 0.76134(11) 0.53866(6) 0.02061(19) Uani 1 1 d . . . S1A S 0.38449(5) 0.66929(4) 0.20928(2) 0.02573(11) Uani 0.9789(14) 1 d PDU A 1 S1B S 0.2696(18) 0.6403(18) 0.1596(9) 0.045(4) Uani 0.0211(14) 1 d PDU A 2 O7 O 0.41558(19) 0.55446(14) 0.14506(7) 0.0412(3) Uani 1 1 d DU . . C18 C 0.3369(4) 0.8373(2) 0.16548(14) 0.0696(9) Uani 1 1 d DU . . H18A H 0.4341 0.8915 0.1435 0.104 Uiso 0.9789(14) 1 calc PR A 1 H18B H 0.2990 0.9082 0.2049 0.104 Uiso 0.9789(14) 1 calc PR A 1 H18C H 0.2512 0.8054 0.1238 0.104 Uiso 0.9789(14) 1 calc PR A 1 H18D H 0.3882 0.8657 0.1174 0.104 Uiso 0.0211(14) 1 calc PR A 2 H18E H 0.4164 0.8654 0.2101 0.104 Uiso 0.0211(14) 1 calc PR A 2 H18F H 0.2449 0.8941 0.1723 0.104 Uiso 0.0211(14) 1 calc PR A 2 C19 C 0.1904(2) 0.6023(2) 0.24175(12) 0.0421(4) Uani 1 1 d DU . . H19A H 0.1939 0.5063 0.2688 0.063 Uiso 0.9789(14) 1 calc PR A 1 H19B H 0.1109 0.5799 0.1968 0.063 Uiso 0.9789(14) 1 calc PR A 1 H19C H 0.1586 0.6835 0.2777 0.063 Uiso 0.9789(14) 1 calc PR A 1 H19D H 0.1521 0.4892 0.2417 0.063 Uiso 0.0211(14) 1 calc PR A 2 H19E H 0.0986 0.6597 0.2482 0.063 Uiso 0.0211(14) 1 calc PR A 2 H19F H 0.2725 0.6351 0.2849 0.063 Uiso 0.0211(14) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01496(8) 0.01668(8) 0.01335(8) 0.00369(6) 0.00305(5) 0.00355(6) Mn1 0.01158(12) 0.01270(12) 0.01175(12) 0.00179(9) 0.00134(9) 0.00124(9) N1 0.0196(5) 0.0173(5) 0.0154(5) 0.0028(4) 0.0013(4) 0.0006(4) N2 0.0202(5) 0.0153(5) 0.0137(5) 0.0028(4) 0.0016(4) 0.0002(4) N3 0.0205(5) 0.0202(5) 0.0155(5) 0.0051(4) 0.0029(4) 0.0018(4) N4 0.0177(5) 0.0200(5) 0.0160(5) 0.0045(4) 0.0035(4) 0.0021(4) C5 0.0185(6) 0.0131(5) 0.0149(6) 0.0019(4) -0.0001(4) -0.0010(5) C1 0.0255(7) 0.0198(6) 0.0129(6) 0.0023(5) 0.0056(5) -0.0004(5) C2 0.0405(9) 0.0275(7) 0.0182(6) -0.0027(5) 0.0047(6) -0.0066(6) C3 0.0255(7) 0.0286(7) 0.0207(6) 0.0027(5) 0.0085(5) 0.0025(6) C4 0.0347(8) 0.0256(7) 0.0207(7) 0.0097(5) 0.0081(6) 0.0041(6) C6 0.0173(6) 0.0127(5) 0.0170(6) 0.0025(4) 0.0011(4) -0.0002(4) N7 0.0165(5) 0.0149(5) 0.0164(5) 0.0032(4) 0.0022(4) 0.0023(4) C8 0.0195(6) 0.0177(6) 0.0199(6) 0.0047(5) 0.0044(5) 0.0029(5) C9 0.0166(6) 0.0177(6) 0.0278(7) 0.0038(5) 0.0053(5) 0.0030(5) C10 0.0167(6) 0.0186(6) 0.0307(7) 0.0050(5) -0.0020(5) 0.0031(5) C11 0.0205(6) 0.0182(6) 0.0215(6) 0.0056(5) -0.0020(5) 0.0012(5) C12 0.0162(6) 0.0284(7) 0.0252(7) -0.0028(5) -0.0006(5) 0.0086(5) C13 0.0123(6) 0.0145(6) 0.0199(6) -0.0031(4) -0.0004(4) 0.0003(4) O1 0.0197(5) 0.0320(5) 0.0224(5) 0.0076(4) 0.0059(4) 0.0108(4) O2 0.0161(4) 0.0299(5) 0.0203(5) 0.0033(4) 0.0036(4) 0.0080(4) C14 0.0265(7) 0.0211(7) 0.0329(8) -0.0040(6) 0.0056(6) -0.0027(6) C15 0.0138(6) 0.0180(6) 0.0189(6) 0.0015(5) -0.0011(4) 0.0040(5) O3 0.0170(4) 0.0246(5) 0.0157(4) -0.0008(3) -0.0011(3) 0.0026(4) O4 0.0241(5) 0.0187(5) 0.0197(5) 0.0015(4) 0.0060(4) 0.0034(4) C16 0.0438(10) 0.0245(8) 0.0330(8) -0.0045(6) 0.0065(7) -0.0097(7) C17 0.0213(6) 0.0162(6) 0.0206(6) 0.0043(5) 0.0000(5) 0.0027(5) O5 0.0228(5) 0.0230(5) 0.0203(5) 0.0029(4) 0.0035(4) -0.0006(4) O6 0.0236(5) 0.0160(4) 0.0227(5) 0.0060(4) 0.0039(4) 0.0019(4) S1A 0.0329(2) 0.0275(2) 0.01810(17) -0.00131(13) 0.00559(14) 0.00891(15) S1B 0.037(10) 0.057(8) 0.037(8) 0.006(8) -0.030(6) 0.005(7) O7 0.0775(10) 0.0314(6) 0.0238(6) 0.0045(5) 0.0175(6) 0.0313(6) C18 0.137(2) 0.0314(10) 0.0575(13) 0.0198(9) 0.0596(15) 0.0409(13) C19 0.0436(10) 0.0268(8) 0.0568(11) 0.0003(8) 0.0162(8) 0.0049(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9480(10) . ? Cu1 O5 1.9526(10) . ? Cu1 O4 1.9639(10) . ? Cu1 N7 2.0652(11) . ? Cu1 N4 2.3486(11) . ? Mn1 O2 2.1252(9) 2_776 ? Mn1 O2 2.1252(9) . ? Mn1 O3 2.1731(9) . ? Mn1 O3 2.1732(9) 2_776 ? Mn1 O6 2.1920(9) 2_776 ? Mn1 O6 2.1920(9) . ? N1 N2 1.3297(16) . ? N1 C5 1.3340(16) . ? N2 N3 1.3214(15) . ? N2 C1 1.4993(16) . ? N3 N4 1.3186(15) . ? N4 C5 1.3453(17) . ? C5 C6 1.4660(18) . ? C1 C4 1.521(2) . ? C1 C2 1.5238(19) . ? C1 C3 1.526(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C6 N7 1.3519(16) . ? C6 C11 1.3850(19) . ? N7 C8 1.3426(17) . ? C8 C9 1.3901(19) . ? C8 H8 0.9500 . ? C9 C10 1.387(2) . ? C9 H9 0.9500 . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.5111(18) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O2 1.2438(16) . ? C13 O1 1.2675(16) . ? C14 C15 1.5047(19) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O3 1.2474(16) . ? C15 O4 1.2725(16) . ? C16 C17 1.5074(19) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 O6 1.2483(17) . ? C17 O5 1.2739(17) . ? S1A O7 1.4949(11) . ? S1A C18 1.764(2) . ? S1A C19 1.7674(19) . ? S1B O7 1.542(15) . ? S1B C19 1.624(15) . ? S1B C18 1.702(15) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C18 H18D 0.9800 . ? C18 H18E 0.9800 . ? C18 H18F 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C19 H19D 0.9800 . ? C19 H19E 0.9800 . ? C19 H19F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O5 90.44(5) . . ? O1 Cu1 O4 89.46(4) . . ? O5 Cu1 O4 175.58(4) . . ? O1 Cu1 N7 177.31(4) . . ? O5 Cu1 N7 92.03(4) . . ? O4 Cu1 N7 88.16(4) . . ? O1 Cu1 N4 101.74(4) . . ? O5 Cu1 N4 93.79(4) . . ? O4 Cu1 N4 90.56(4) . . ? N7 Cu1 N4 77.04(4) . . ? O2 Mn1 O2 179.999(1) 2_776 . ? O2 Mn1 O3 87.80(4) 2_776 . ? O2 Mn1 O3 92.20(4) . . ? O2 Mn1 O3 92.20(4) 2_776 2_776 ? O2 Mn1 O3 87.80(4) . 2_776 ? O3 Mn1 O3 180.0 . 2_776 ? O2 Mn1 O6 93.88(4) 2_776 2_776 ? O2 Mn1 O6 86.12(4) . 2_776 ? O3 Mn1 O6 85.30(4) . 2_776 ? O3 Mn1 O6 94.70(4) 2_776 2_776 ? O2 Mn1 O6 86.12(4) 2_776 . ? O2 Mn1 O6 93.88(4) . . ? O3 Mn1 O6 94.70(4) . . ? O3 Mn1 O6 85.30(4) 2_776 . ? O6 Mn1 O6 180.00(5) 2_776 . ? N2 N1 C5 101.32(11) . . ? N3 N2 N1 114.10(10) . . ? N3 N2 C1 122.22(11) . . ? N1 N2 C1 123.61(11) . . ? N4 N3 N2 105.84(11) . . ? N3 N4 C5 106.43(10) . . ? N3 N4 Cu1 147.04(9) . . ? C5 N4 Cu1 106.52(8) . . ? N1 C5 N4 112.30(11) . . ? N1 C5 C6 125.82(12) . . ? N4 C5 C6 121.88(11) . . ? N2 C1 C4 108.00(11) . . ? N2 C1 C2 107.35(11) . . ? C4 C1 C2 111.54(12) . . ? N2 C1 C3 107.62(11) . . ? C4 C1 C3 110.54(12) . . ? C2 C1 C3 111.60(12) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N7 C6 C11 122.56(12) . . ? N7 C6 C5 115.29(11) . . ? C11 C6 C5 122.15(12) . . ? C8 N7 C6 118.11(11) . . ? C8 N7 Cu1 122.61(9) . . ? C6 N7 Cu1 118.81(9) . . ? N7 C8 C9 122.48(12) . . ? N7 C8 H8 118.8 . . ? C9 C8 H8 118.8 . . ? C10 C9 C8 118.99(13) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C11 C10 C9 118.89(12) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C6 C11 C10 118.96(12) . . ? C6 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 O1 125.69(12) . . ? O2 C13 C12 118.30(12) . . ? O1 C13 C12 116.01(12) . . ? C13 O1 Cu1 126.16(9) . . ? C13 O2 Mn1 142.11(9) . . ? C15 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O3 C15 O4 123.64(12) . . ? O3 C15 C14 119.53(12) . . ? O4 C15 C14 116.84(12) . . ? C15 O3 Mn1 143.37(9) . . ? C15 O4 Cu1 110.61(8) . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O6 C17 O5 123.37(12) . . ? O6 C17 C16 119.39(13) . . ? O5 C17 C16 117.23(12) . . ? C17 O5 Cu1 111.24(9) . . ? C17 O6 Mn1 141.38(9) . . ? O7 S1A C18 107.22(9) . . ? O7 S1A C19 107.49(9) . . ? C18 S1A C19 97.94(12) . . ? O7 S1B C19 112.7(9) . . ? O7 S1B C18 108.2(9) . . ? C19 S1B C18 106.5(9) . . ? S1A O7 S1B 47.9(6) . . ? S1B C18 H18A 127.3 . . ? S1A C18 H18A 109.5 . . ? S1B C18 H18B 121.1 . . ? S1A C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? S1B C18 H18C 67.9 . . ? S1A C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? S1B C18 H18D 109.5 . . ? S1A C18 H18D 118.3 . . ? H18B C18 H18D 127.2 . . ? H18C C18 H18D 75.2 . . ? S1B C18 H18E 109.5 . . ? S1A C18 H18E 68.3 . . ? H18A C18 H18E 75.2 . . ? H18B C18 H18E 68.2 . . ? H18C C18 H18E 175.4 . . ? H18D C18 H18E 109.5 . . ? S1B C18 H18F 109.5 . . ? S1A C18 H18F 130.0 . . ? H18A C18 H18F 118.2 . . ? H18C C18 H18F 68.6 . . ? H18D C18 H18F 109.5 . . ? H18E C18 H18F 109.5 . . ? S1B C19 H19A 125.7 . . ? S1A C19 H19A 109.5 . . ? S1B C19 H19B 67.1 . . ? S1A C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? S1B C19 H19C 122.9 . . ? S1A C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? S1B C19 H19D 109.5 . . ? S1A C19 H19D 119.7 . . ? H19B C19 H19D 76.1 . . ? H19C C19 H19D 125.4 . . ? S1B C19 H19E 109.5 . . ? S1A C19 H19E 128.9 . . ? H19A C19 H19E 119.3 . . ? H19B C19 H19E 68.5 . . ? H19D C19 H19E 109.5 . . ? S1B C19 H19F 109.5 . . ? S1A C19 H19F 67.4 . . ? H19A C19 H19F 76.2 . . ? H19B C19 H19F 174.4 . . ? H19C C19 H19F 68.2 . . ? H19D C19 H19F 109.5 . . ? H19E C19 H19F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 N2 N3 -0.65(14) . . . . ? C5 N1 N2 C1 -177.83(11) . . . . ? N1 N2 N3 N4 0.66(14) . . . . ? C1 N2 N3 N4 177.89(11) . . . . ? N2 N3 N4 C5 -0.36(13) . . . . ? N2 N3 N4 Cu1 178.23(12) . . . . ? O1 Cu1 N4 N3 6.20(17) . . . . ? O5 Cu1 N4 N3 -85.04(16) . . . . ? O4 Cu1 N4 N3 95.76(16) . . . . ? N7 Cu1 N4 N3 -176.25(17) . . . . ? O1 Cu1 N4 C5 -175.22(8) . . . . ? O5 Cu1 N4 C5 93.54(8) . . . . ? O4 Cu1 N4 C5 -85.66(8) . . . . ? N7 Cu1 N4 C5 2.33(8) . . . . ? N2 N1 C5 N4 0.40(14) . . . . ? N2 N1 C5 C6 -179.86(12) . . . . ? N3 N4 C5 N1 -0.03(15) . . . . ? Cu1 N4 C5 N1 -179.23(8) . . . . ? N3 N4 C5 C6 -179.78(11) . . . . ? Cu1 N4 C5 C6 1.02(14) . . . . ? N3 N2 C1 C4 143.46(12) . . . . ? N1 N2 C1 C4 -39.57(16) . . . . ? N3 N2 C1 C2 -96.14(15) . . . . ? N1 N2 C1 C2 80.82(15) . . . . ? N3 N2 C1 C3 24.11(16) . . . . ? N1 N2 C1 C3 -158.93(12) . . . . ? N1 C5 C6 N7 174.45(12) . . . . ? N4 C5 C6 N7 -5.83(17) . . . . ? N1 C5 C6 C11 -5.8(2) . . . . ? N4 C5 C6 C11 173.95(12) . . . . ? C11 C6 N7 C8 0.65(18) . . . . ? C5 C6 N7 C8 -179.57(11) . . . . ? C11 C6 N7 Cu1 -171.70(10) . . . . ? C5 C6 N7 Cu1 8.09(14) . . . . ? O5 Cu1 N7 C8 88.82(10) . . . . ? O4 Cu1 N7 C8 -86.76(10) . . . . ? N4 Cu1 N7 C8 -177.76(11) . . . . ? O5 Cu1 N7 C6 -99.20(9) . . . . ? O4 Cu1 N7 C6 85.23(9) . . . . ? N4 Cu1 N7 C6 -5.77(9) . . . . ? C6 N7 C8 C9 -0.78(19) . . . . ? Cu1 N7 C8 C9 171.26(10) . . . . ? N7 C8 C9 C10 0.4(2) . . . . ? C8 C9 C10 C11 0.2(2) . . . . ? N7 C6 C11 C10 -0.1(2) . . . . ? C5 C6 C11 C10 -179.87(12) . . . . ? C9 C10 C11 C6 -0.3(2) . . . . ? O2 C13 O1 Cu1 -1.19(19) . . . . ? C12 C13 O1 Cu1 178.72(9) . . . . ? O5 Cu1 O1 C13 -85.90(11) . . . . ? O4 Cu1 O1 C13 89.68(11) . . . . ? N4 Cu1 O1 C13 -179.86(11) . . . . ? O1 C13 O2 Mn1 -0.8(2) . . . . ? C12 C13 O2 Mn1 179.33(10) . . . . ? O3 Mn1 O2 C13 -46.66(15) . . . . ? O3 Mn1 O2 C13 133.34(15) 2_776 . . . ? O6 Mn1 O2 C13 -131.79(15) 2_776 . . . ? O6 Mn1 O2 C13 48.21(15) . . . . ? O4 C15 O3 Mn1 63.7(2) . . . . ? C14 C15 O3 Mn1 -115.99(15) . . . . ? O2 Mn1 O3 C15 -179.30(15) 2_776 . . . ? O2 Mn1 O3 C15 0.70(15) . . . . ? O6 Mn1 O3 C15 86.62(15) 2_776 . . . ? O6 Mn1 O3 C15 -93.38(15) . . . . ? O3 C15 O4 Cu1 -5.42(16) . . . . ? C14 C15 O4 Cu1 174.28(10) . . . . ? O1 Cu1 O4 C15 -95.91(9) . . . . ? N7 Cu1 O4 C15 85.34(9) . . . . ? N4 Cu1 O4 C15 162.36(9) . . . . ? O6 C17 O5 Cu1 0.40(17) . . . . ? C16 C17 O5 Cu1 179.27(11) . . . . ? O1 Cu1 O5 C17 100.93(9) . . . . ? N7 Cu1 O5 C17 -80.14(9) . . . . ? N4 Cu1 O5 C17 -157.28(9) . . . . ? O5 C17 O6 Mn1 -61.3(2) . . . . ? C16 C17 O6 Mn1 119.86(15) . . . . ? O2 Mn1 O6 C17 -178.30(15) 2_776 . . . ? O2 Mn1 O6 C17 1.70(15) . . . . ? O3 Mn1 O6 C17 94.23(14) . . . . ? O3 Mn1 O6 C17 -85.77(14) 2_776 . . . ? C18 S1A O7 S1B -54.8(7) . . . . ? C19 S1A O7 S1B 49.6(7) . . . . ? C19 S1B O7 S1A -59.0(7) . . . . ? C18 S1B O7 S1A 58.4(7) . . . . ? O7 S1B C18 S1A -53.7(6) . . . . ? C19 S1B C18 S1A 67.7(7) . . . . ? O7 S1A C18 S1B 55.8(8) . . . . ? C19 S1A C18 S1B -55.4(8) . . . . ? O7 S1B C19 S1A 52.9(7) . . . . ? C18 S1B C19 S1A -65.5(7) . . . . ? O7 S1A C19 S1B -52.7(8) . . . . ? C18 S1A C19 S1B 58.2(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C3 H3B O7 0.98 2.48 3.4176(19) 161. 1_556 C3 H3C O7 0.98 2.41 3.3042(18) 151. 2_666 C8 H8 O6 0.95 2.55 3.1590(17) 123. . C10 H10 O7 0.95 2.54 3.2926(18) 136. 2_766 C18 H18B O1 0.98 2.45 3.338(2) 151. 2_676 C19 H19A O5 0.98 2.48 3.449(2) 168. 2_666 C19 H19E O4 0.98 2.46 3.375(2) 156. 2_676 C12 H12B S1A 0.98 2.86 3.7750(14) 156. 2_676 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.451 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.051